[ CAS No. 123387-72-4 ] {[proInfo.proName]}

Name: 123387-72-4|tert-Butyl methyl(2-oxoethyl)carbamate|95%
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Quality Control of [ 123387-72-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 123387-72-4 ]

Product Details of [ 123387-72-4 ]

CAS No. :	123387-72-4	MDL No. :	MFCD08064267
Formula :	C₈H₁₅NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MSWTVSDFEYSRMQ-UHFFFAOYSA-N
M.W :	173.21	Pubchem ID :	10725881
Synonyms :

Calculated chemistry of [ 123387-72-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.38
TPSA :	46.61 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	0.64
Log Po/w (WLOGP) :	1.05
Log Po/w (MLOGP) :	0.53
Log Po/w (SILICOS-IT) :	0.24
Consensus Log Po/w :	0.86

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.99
Solubility :	17.8 mg/ml ; 0.103 mol/l
Class :	Very soluble
Log S (Ali) :	-1.19
Solubility :	11.1 mg/ml ; 0.064 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.85
Solubility :	24.3 mg/ml ; 0.14 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 123387-72-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 123387-72-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 123387-72-4 ]
Downstream synthetic route of [ 123387-72-4 ]

[ 123387-72-4 ] Synthesis Path-Upstream 1~9

1
[ 57561-39-4 ]
[ 123387-72-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 3 h;	(a) tert-Butyl methyl(2-oxoethyl) carbamate; Dess-Martin periodinane (22 g, 52 mmol) was added in portions to 2-(N-Boc- methylamino)ethanol (8.8 g, 50 mmol) in dicholoromethane at O⁰C. The mixture was allowed to reach r.t. and stirred for 3h. Saturated solutions of aqueous sodium hydrogencarbonate and sodium thiosulfate were added and the resulting solution stirred for 0.5 h. The organic phase was separated and washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate and concentrated to give 9 g (quantitative yield) of the title compound. GC-MS m/z 174 (M +1).
98%	With Dess-Martin periodane In dichloromethane at 20℃; for 3 h; Inert atmosphere	To an ice-cooled solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (300mg, 1 .71 mmol)) in dry CH₂CI₂ (8.5ml_) under argon was added portion wise Dess-Martin periodinane (762mg, 1.8mmol). Once finished the addition, the reaction mixture was stirred at room temperature for 3h. The mixture was poured into saturated solutions of NaHCOs (50 mL) and Na₂S₂0₃ (50 mL) and more CH₂CI₂ (100 mL). It was well-stirred at room temperature for 30 minutes. The organic phase was separated and washed with sat. aq. NaHC0₃ (1 x 20 mL). It was dried over magnesium sulphate and concentrated to afford the title compound (370 mg, 98percent) as colourless oil together with a yellow solid, which was used in the next step without further purification.¹H NMR (300 MHz, cdcl3) δ 9.61 (s, 1 H), 3.98 (d, J = 33.9 Hz, 2H), 2.94 (t, J = 10.8 Hz, 3H), 1 .46 (dd, J = 8.2, 6.3 Hz, 9H).
74%	Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 0.166667 h; Stage #2: With triethylamine In dichloromethane at -60℃; for 0.5 h;	Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 °C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 °C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 °C) and stirred an additional 10 min. 40 ml (285 mmol) Et₃N was added dropwise followed by 50 ml DCM (T < -60 °C) and stirred for 30 min. The reaction mixture was warmed to 0 °C and washed with 3x100 ml water, 100 ml 0.5 M KHS0₄, 75 ml brine, dried with MgS0₄ and concentrated in vacuo. The product was purified by column chromatography (Si0₂, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74percent) of compound 1. 1H-NMR (300MHz, CDC1₃): δ = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH₂), 9.60 (s, 1H, CHO). Z/E isomers.

200 g

Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at 65℃; for 1 h; Inert atmosphere
Stage #2: With triethylamine In dichloromethane at -70℃; for 3 h; Inert atmosphere

A flame-dried 3 L, 3-neck round bottom flask containing a mechanical stirrer (central port), internal temperature probe and addition funnel was charged with oxalyl chloride (176 mL, 2.01 mol) and CH₂Cl₂ (634 mL). The flask was cooled to -70 °C and DMSO (286 mL, 4.02 mol) was added over 2.5 h at a rate that maintained an internal temperature below -65 °C. The mixture was then stirred for an additional 15 min, after which tert-butyl 2-hydroxyethyl(methyl)carbamate¹² (235 g, 1.34 mol) in CH₂Cl₂ (700 mL) was added over 1 h, followed by slow addition of Et₃N (841 mL, 6.04 mol) over 30 min. Both of these reactants were added at a rate that did not cause an increase in internal temperature. After addition of the alcohol solution the reaction was cloudy. Upon initial addition of Et₃N the reaction became colorless/clear however at the end the reaction was milky white. The reaction was monitored by TLC (Hex/EtOAc 1:1) until the reaction was deemed complete (2.5 h additional, -70 °C). Saturated aqueous sodium bicarbonate solution (500 mL) was then introduced to quench the reaction at -78 °C. (Note: Quenching is fairly exothermic and thus should be done slowly.) The reaction was warmed to rt and the phases were separated. The combined organics were washed with water, dried over MgSO₄, and concentrated (upon concentration, some small amounts of precipitate (presumably Et₃N/HCl salt) were observed however this small amount did not impede distillation or effect final purity.) Distillation (87-89 °C, 3 mmHg) provided aldehyde 2 (200 g, 128 mmol) as a colorless oil, which matched all data reported by Kato and co-workers.¹²

Reference： [1] Patent: WO2007/120098, 2007, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2013/68552, 2013, A1, . Location in patent: Page/Page column 53
[3] ChemMedChem, 2015, vol. 10, # 3, p. 470 - 489
[4] Patent: WO2011/133039, 2011, A2, . Location in patent: Page/Page column 202
[5] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 21, p. 3219 - 3225
[6] Patent: WO2006/135316, 2006, A1, . Location in patent: Page/Page column 124-125
[7] Patent: WO2009/29439, 2009, A1, . Location in patent: Page/Page column 16
[8] Journal of the American Chemical Society, 2010, vol. 132, # 47, p. 16962 - 16976
[9] Patent: EP2287173, 2011, A1, . Location in patent: Page/Page column 43
[10] Tetrahedron, 2011, vol. 67, # 34, p. 6131 - 6137
[11] Patent: WO2013/68554, 2013, A1, . Location in patent: Page/Page column 63

2
[ 140170-90-7 ]
[ 123387-72-4 ]

Reference： [1] European Journal of Medicinal Chemistry, 1991, vol. 26, # 9, p. 921 - 928
[2] Tetrahedron, 2002, vol. 58, # 9, p. 1719 - 1737
[3] Journal of Natural Products, 2003, vol. 66, # 2, p. 183 - 199
[4] Patent: US2006/235037, 2006, A1, . Location in patent: Page/Page column 19

3
[ 24424-99-5 ]
[ 123387-72-4 ]

Reference： [1] Helvetica Chimica Acta, 2006, vol. 89, # 8, p. 1559 - 1573
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 21, p. 3219 - 3225
[3] Tetrahedron, 2011, vol. 67, # 34, p. 6131 - 6137
[4] Patent: WO2011/133039, 2011, A2,
[5] ChemMedChem, 2015, vol. 10, # 3, p. 470 - 489

4
[ 13734-36-6 ]
[ 123387-72-4 ]

Reference： [1] Journal of Natural Products, 2003, vol. 66, # 2, p. 183 - 199
[2] Tetrahedron, 2002, vol. 58, # 9, p. 1719 - 1737
[3] European Journal of Medicinal Chemistry, 1991, vol. 26, # 9, p. 921 - 928

5
[ 79-37-8 ]
[ 57561-39-4 ]
[ 121-44-8 ]
[ 123387-72-4 ]

Reference： [1] Patent: US5888972, 1999, A,

6
[ 462655-19-2 ]
[ 123387-72-4 ]

Reference： [1] Helvetica Chimica Acta, 2006, vol. 89, # 8, p. 1559 - 1573

7
[ 42492-57-9 ]
[ 123387-72-4 ]

Reference： [1] Journal of Natural Products, 2003, vol. 66, # 2, p. 183 - 199

8
[ 16066-84-5 ]
[ 123387-72-4 ]

Reference： [1] Helvetica Chimica Acta, 2006, vol. 89, # 8, p. 1559 - 1573

9
[ 7541-17-5 ]
[ 68-12-2 ]
[ 123387-72-4 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 10, p. 1197 - 1200

[ 123387-72-4 ] Synthesis Path-Downstream 1~27

1
[ 57561-39-4 ]
[ 123387-72-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 3h;	(a) tert-Butyl methyl(2-oxoethyl) carbamate; Dess-Martin periodinane (22 g, 52 mmol) was added in portions to 2-(N-Boc- methylamino)ethanol (8.8 g, 50 mmol) in dicholoromethane at O0C. The mixture was allowed to reach r.t. and stirred for 3h. Saturated solutions of aqueous sodium hydrogencarbonate and sodium thiosulfate were added and the resulting solution stirred for 0.5 h. The organic phase was separated and washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate and concentrated to give 9 g (quantitative yield) of the title compound. GC-MS m/z 174 (M +1).
98%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3h;Inert atmosphere;	To an ice-cooled solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (300mg, 1 .71 mmol)) in dry CH2CI2 (8.5ml_) under argon was added portion wise Dess-Martin periodinane (762mg, 1.8mmol). Once finished the addition, the reaction mixture was stirred at room temperature for 3h. The mixture was poured into saturated solutions of NaHCOs (50 mL) and Na2S203 (50 mL) and more CH2CI2 (100 mL). It was well-stirred at room temperature for 30 minutes. The organic phase was separated and washed with sat. aq. NaHC03 (1 x 20 mL). It was dried over magnesium sulphate and concentrated to afford the title compound (370 mg, 98%) as colourless oil together with a yellow solid, which was used in the next step without further purification.1H NMR (300 MHz, cdcl3) delta 9.61 (s, 1 H), 3.98 (d, J = 33.9 Hz, 2H), 2.94 (t, J = 10.8 Hz, 3H), 1 .46 (dd, J = 8.2, 6.3 Hz, 9H).
74%		Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 C) and stirred an additional 10 min. 40 ml (285 mmol) Et3N was added dropwise followed by 50 ml DCM (T < -60 C) and stirred for 30 min. The reaction mixture was warmed to 0 C and washed with 3x100 ml water, 100 ml 0.5 M KHS04, 75 ml brine, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74%) of compound 1. 1H-NMR (300MHz, CDC13): delta = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH2), 9.60 (s, 1H, CHO). Z/E isomers.

		Example 6 tert-Butyl ('2-(7-r2-r4-cvanophenoxy>>ethyll-9-oxa-3.7-diazabicvclo[3.3.11non-3- yl } ethyDmethylcarbamateOxalyl chloride (0.544 g, 0.4 mrnol) was added at -78C to a solution of DMSO (0.7 g, 0.9 mmol) in dry dichloromethane (10 mL). The resulting mixture was EPO <DP n="126"/>stirred for 15 min before tert-butyl (2-hydroxyethyl)methylcarbamate (0.5 g,0.3 mmol; prepared by reaction of 2-methylaminoethanol with di-tert-butyl dicarbonate under standard conditions, using DCM as solvent), dissolved in dry dichloromethane, was added dropwise at -78C. Stirring was continued for 3 h at the same temperature, before triethylamine was added (at -78C) and the reaction mixture was warmed to -3O0C. The reaction was quenched with citric acid solution and extracted with dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Solvent evaporation yielded (0.35 g) of crude aldehyde (tert-butyl (2-oxoethyl)methylcarbamate). The crude aldehyde was then taken in DCM (10 mL). 4-[2-(9-Oxa-3,7- diazabicyclo[3.3.1]non-3-yl)ethoxy]benzonitrile (0.221 g, 0.8 mmol; see WO 01/28992), followed by acetic acid (0.182 g, 0.3 mmol), was added. After stirring for 1 h, NaBH3CN (0.188 g, 0.3 mmol) was added. The reaction mixture was stirred at RT overnight, quenched with water and extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification by column chromatography over silica gel using 2.5% methanol in dichloromethane as eluent, yielded 80 mg of the title compound as a pale yellow, gummy liquid. 1H NMR (300 MHz, CDCl3): delta 7.58 (2H, dd), 7.00 (2H5 dd), 4.33 (2H, t) 4.20 (2H, bs), 3.79 (2H, b), 3.58 (2H, m), 3.35 (2H, d), 3.23 (2H, d), 3.1 (6H, m), 2.92 (3H5 s), 1.41(9H, s).
	With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 20℃;	Combine under a nitrogen atmosphere, dichloromethane (37.91 moles;2.43 L), dimethyl sulfoxide (7.30 moles; 518.4 mL), triethylamine (1.85 moles; 257.7 mL), and (2-hydroxy-ethyl)-methyl-carbamic acid t-butyl ester (924.5 mmoles; 162.0 g). Add in steps sulfur trioxide:pyridine complex (1.849 moles; 300.3 g), maintaining the reaction temperature less than 20 0C. Stir the reaction mixture at ambient temperature overnight. Add 1.0 L water, separate the organic layer, wash with 10% citric acid in water (80OmL), water and brine. Concentrate and pass through a silica plug, eluting with 20% ethyl acetate/hexanes. Add toluene (200 mL) and concentrate to provide the title intermediate (yield 62.45%, 100 g).
	With Dess-Martin periodane; In chloroform; at 20℃; for 1.5h;Cooling with ice;	(1) t-Butyl (2-hydroxyethyl)methylcarbamate (1.0 g) obtained by the method described in the literature (Synthetic Communications, 1993, p.2443) was dissolved in chloroform (5 ml), and a Dess-Martin reagent (2.54 g) was added to the solution under ice cooling. The resulting mixture was stirred at room temperature for 1.5 hours, then saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate were added to the reaction mixture, and the resulting mixture was stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain an aldehyde compound (1.21 g).
200 g		A flame-dried 3 L, 3-neck round bottom flask containing a mechanical stirrer (central port), internal temperature probe and addition funnel was charged with oxalyl chloride (176 mL, 2.01 mol) and CH2Cl2 (634 mL). The flask was cooled to -70 C and DMSO (286 mL, 4.02 mol) was added over 2.5 h at a rate that maintained an internal temperature below -65 C. The mixture was then stirred for an additional 15 min, after which tert-butyl 2-hydroxyethyl(methyl)carbamate12 (235 g, 1.34 mol) in CH2Cl2 (700 mL) was added over 1 h, followed by slow addition of Et3N (841 mL, 6.04 mol) over 30 min. Both of these reactants were added at a rate that did not cause an increase in internal temperature. After addition of the alcohol solution the reaction was cloudy. Upon initial addition of Et3N the reaction became colorless/clear however at the end the reaction was milky white. The reaction was monitored by TLC (Hex/EtOAc 1:1) until the reaction was deemed complete (2.5 h additional, -70 C). Saturated aqueous sodium bicarbonate solution (500 mL) was then introduced to quench the reaction at -78 C. (Note: Quenching is fairly exothermic and thus should be done slowly.) The reaction was warmed to rt and the phases were separated. The combined organics were washed with water, dried over MgSO4, and concentrated (upon concentration, some small amounts of precipitate (presumably Et3N/HCl salt) were observed however this small amount did not impede distillation or effect final purity.) Distillation (87-89 C, 3 mmHg) provided aldehyde 2 (200 g, 128 mmol) as a colorless oil, which matched all data reported by Kato and co-workers.12
	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3h;Inert atmosphere; Cooling with ice;	Intermediate 34.ferf-butyl methyl(2-oxoethyl)carbamateTo an ice-cooled solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (300mg, 1 .71 mmol)) in dry CH2CI2 (8.5ml_) under argon was added portion wise Dess-Martin periodinane (762mg, 1.8mmol). Once finished the addition, the reaction mixture was stirred at room temperature for 3h. The mixture was poured into saturated solutions of NaHCOs (50 mL) and Na2S203 (50 mL) and more CH2CI2 (100 mL). It was well-stirred at room temperature for 30 minutes. The organic phase was separated and washed with sat. aq. NaHC03 (1 x 20 mL). It was dried over magnesium sulphate and concentrated to afford the title compound (370 mg, 98%) as colourless oil together with a yellow solid, which was used in the next step without further purification.1H NMR (300 MHz, cdcl3) delta 9.61 (s, 1 H), 3.98 (d, J = 33.9 Hz, 2H), 2.94 (t, J = 10.8 Hz, 3H), 1 .46 (dd, J = 8.2, 6.3 Hz, 9H).
8.65 g	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃;Inert atmosphere;	Compound 20 (10 g, 57 mmol)Soluble in 250mL of dry dichloromethane,Nitrogen bubbling,Dess-Martin oxidant (DMP, 26.6 g) was added in portions at 0 C.Add the room temperature reaction,TLC (PE/EA = 1/1) monitors the progress of the reaction.Post-processing,Add 500 mL of saturated sodium bicarbonate solution,500mL saturated aqueous sodium thiosulfate solution andStir in 800 mL of dichloromethane for 30 min.Layered, the organic layer is saturated with sodium bicarbonate,Saturated with sodium chloride,Dry over anhydrous sodium sulfate, filter,Concentration under reduced pressure gave a white oil, 8.65 g.
	With Dess-Martin periodane; In dichloromethane; at 20 - 30℃; for 1h;Inert atmosphere;	2-(Boc-methyl-amino)-ethanol (0.19 g, 1 mmol) was dissolved in 4 mL of dichloromethane, and added with Dess-Martin periodinane (0.64 g, 1.5 mmol), and stirred at room temperature for 1 hour. 3 mL of a saturated sodium thiosulfate solution and 5 mL of a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was stirred until clarified. Then, it was extracted with 20 mL of dichloromethane, and the dichloromethane layer was concentrated under reduced pressure. The residues were dissolved in 5 mL of acetic acid, and added with ethyl 5-bromo-3-amino-2-methyl-benzoate 1c (0.26 g, 1 mmol). The sodium borohydride (0.22 g, 6 mmol) was added portionwise and then stirred at room temperature for 0.5 hour. The reaction solution was added with water and ethyl acetate. The ethyl acetate layer was washed with aqueous solution of sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residues were purified by column chromatography (eluent: petroleum ether:ethyl acetate 30:1 to 3:1) to give 0.3 g of title product.

Reference： [1]Patent: WO2007/120098,2007,A1 .Location in patent: Page/Page column 88
[2]Patent: WO2013/68552,2013,A1 .Location in patent: Page/Page column 53
[3]ChemMedChem,2015,vol. 10,p. 470 - 489
[4]Bioorganic and Medicinal Chemistry,2020,vol. 28
[5]Patent: WO2011/133039,2011,A2 .Location in patent: Page/Page column 202
[6]Journal of the Chemical Society. Perkin transactions I,1997,p. 3219 - 3225
[7]Patent: WO2006/135316,2006,A1 .Location in patent: Page/Page column 124-125
[8]Patent: WO2009/29439,2009,A1 .Location in patent: Page/Page column 16
[9]Journal of the American Chemical Society,2010,vol. 132,p. 16962 - 16976
[10]Patent: EP2287173,2011,A1 .Location in patent: Page/Page column 43
[11]Tetrahedron,2011,vol. 67,p. 6131 - 6137
[12]Patent: WO2013/68554,2013,A1 .Location in patent: Page/Page column 63
[13]Patent: CN109106951,2019,A .Location in patent: Paragraph 0145; 0146; 0147; 0148
[14]Patent: US2019/345139,2019,A1 .Location in patent: Paragraph 0596-0597

2
[ 123387-72-4 ]
[ 146476-37-1 ]
[ 913963-45-8 ]

Reference： [1]Helvetica Chimica Acta,2006,vol. 89,p. 1559 - 1573

3
[ 16066-84-5 ]
[ 123387-72-4 ]

Reference： [1]Helvetica Chimica Acta,2006,vol. 89,p. 1559 - 1573

4
[ 42492-57-9 ]
[ 123387-72-4 ]

Reference： [1]Journal of Natural Products,2003,vol. 66,p. 183 - 199

5
[ 123387-72-4 ]
[ 50461-59-1 ]
[ 1234206-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h;	Amine F-57: 1-(2-Methylamino-ethyl)-4-pyridin-3-yl-piperidin-4-ol hydrochloride Stage 1: Methyl-(2-oxo-ethyl)-carbamic acid tert-butyl ester (2 equiv.), acetic acid (3 equiv.) and triacetoxy borohydride (3 equiv.) were added to a solution of F-16 in dichloromethane (5 ml/mmol); the mixture was stirred for 12 hours at room temperature and then diluted with dichloromethane. The reaction mixture was washed with saturated sodium hydrogen carbonate solution and saturated NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (10% methanol in dichloromethane).

Reference： [1]Patent: US2010/173889,2010,A1 .Location in patent: Page/Page column 64

6
[ 224178-65-8 ]
[ 123387-72-4 ]
C₁₈H₂₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12.0h;	Stage 3: Methyl-(2-oxo-ethyl)-carbamic acid tert-butyl ester (2 equiv.), acetic acid (3 equiv.) and triacetoxy borohydride (3 equiv.) were added to a solution of the amine obtained above in dichloromethane (5 ml/mmol); the mixture was stirred for 12 hours at RT and then diluted with dichloromethane. the reaction mixture was washed with saturated sodium hydrogen carbonate solution and saturated NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (10% MeOH in dichloromethane).

Reference： [1]Patent: US2010/173889,2010,A1 .Location in patent: Page/Page column 63-64

7
[ 867-13-0 ]
[ 123387-72-4 ]
[ 149650-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil for 0.166667h; Inert atmosphere; Stage #2: O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere;

Reference： [1]Hanessian, Stephen; Stoffman, Eli; Mi, Xueling; Renton, Paul [Organic Letters, 2011, vol. 13, # 5, p. 840 - 843]

8
[ 876461-55-1 ]
[ 57561-39-4 ]
[ 123387-72-4 ]
benzyl (3S)-3-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of the crude product of <strong>[876461-55-1]benzyl (3S)-3-aminopiperidine-1-carboxylate</strong> (107 mg) and tert-butyl N-methyl-N-(2-oxoethyl)carbamate (59.3 mg, 0.343 mmol) in DCM (2.1 ml) was cooled to 0C, followed by addition of sodium triacetoxyborohydride (145 mg, 0.685 mmol), and it was stirred at 0C. After 30 minutes, tert-butyl N-methyl-N-(2-oxoethyl)carbamate (6.0 mg, 0.035 mmol) was added, and the mixture was stirred at 0C for 30 more minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. After the drying agent was removed by filtration, a crude product of benzyl (3S)-3-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]piperidine-1-carboxylate (169 mg) was obtained as a yellow oily substance by concentration under reduced pressure. LCMS: m/z 392 [M+H]+

Reference： [1]Patent: EP2842946,2015,A1 .Location in patent: Paragraph 1687

9
[ 876461-55-1 ]
[ 123387-72-4 ]
benzyl (3S)-3-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In chloroform; at 0℃; for 1h;	A solution of the crude product of <strong>[876461-55-1]benzyl (3S)-3-aminopiperidine-1-carboxylate</strong> (107 mg) and tert-butyl N-methyl-N-(2-oxoethyl)carbamate (59.3 mg, 0.343 mmol) in chloroform (2.1 ml) was cooled to 0C, followed by addition of sodium triacetoxyborohydride (145 mg, 0.685 mmol), and it was stirred at 0C. After 30 minutes, tert-butyl N-methyl-N-(2-oxoethyl)carbamate (6.0 mg, 0.035 mmol) was added, and the mixture was stirred at 0C for 30 more minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. After the drying agent was removed by filtration, a crude product of benzyl (3S)-3-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]piperidine-1-carboxylate (169 mg) was obtained as a yellow oily substance by concentration under reduced pressure. LCMS: m/z 392 [M+H]+ HPLC retention time: 0.51 min (analysis condition F)

Reference： [1]Patent: EP2842939,2015,A1 .Location in patent: Paragraph 1625

10
[ 581065-95-4 ]
[ 123387-72-4 ]
N-[(PEG)4COO-t-Bu]-N’-Boc-N’-methylethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.5%		[00225j Synthesis of N- [(PEG)4C00-t-Buj -N?-Boc-N?-methyl-ethylenediamine .To the solution of <strong>[581065-95-4]N-t-BuOOC-(PEG)4-amine</strong> (0.557g , 1.73 mmol) in 20 ml of methanol, (N-methyl)N-Boc acetaldehyde (0.3 g, 1.73 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (0.196g, 5.2 mmol) was added to the mixture at 0C, and the resultant mixture was stirred at 0C for 1 hour and 1 hour at room temperature. The reaction was quenched by adding 5 ml of water. After removal of solvent, 5 ml of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4, and the product was purified by flash silica chromatography using heptane/ethyl acetate to methylene chloride/methanol to give a yield of 64.5% (0.535 g). ?H NMR (300 MHz, CD2C12) 3 ppm: 3.5-3.8 (m, 18H, CH2), 3.45 (br, 2H, CH2), 2.98 (br, 2H, CH2), 2.83 (s, 3H, NCH3), 2.46 (t, 2H, COCH2), 1.42 (s, 18H, CH3); MS-ESI (mle): 479.6 [M+H].
64.5%		To a solution of <strong>[581065-95-4]N-t-BuOOC-(PEG)4-amine</strong> (0.557 g, 1.73 mmol) in 20 mL of methanol, (N-methyl)-N-Boc acetaldehyde (0.3 g, 1.73 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (0.196 g, 5.2 mmol) was added to the mixture at 0 C., and the resultant mixture was stirred at 0 C. for 1 hour and then 1 hour at room temperature. The reaction was quenched by adding 5 mL of water. After removal of solvent, 5 mL of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4, and the product was purified by flash silica chromatography using heptane/ethyl acetate to methylene chloride/methanol to give a yield of 64.5% (0.535 g). 1H NMR (300 MHz, CD2Cl2) delta ppm: 3.5-3.8 (m, 18H, CH2), 3.45 (br, 2H, CH2), 2.98 (br, 2H, CH2), 2.83 (s, 3H, NCH3), 2.46 (t, 2H, COCH2), 1.42 (s, 18H, CH3); MS-ESI (m/e): 479.6 [M+H].

Reference： [1]Patent: WO2015/116867,2015,A1 .Location in patent: Paragraph 00225
[2]Patent: US2020/30456,2020,A1 .Location in patent: Paragraph 0246-0247

11
[ 581065-95-4 ]
[ 123387-72-4 ]
N-[(PEG)4COO-t-Bu]-N’-Boc-N‘-methyl-ethylenediamine furimazine carbamate [ No CAS ]

Reference： [1]Patent: WO2015/116867,2015,A1

12
[ 252881-74-6 ]
[ 123387-72-4 ]
N-[(PEG)3-COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		[00229j Synthesis of N- [(PEG)3-COO-t-Buj -N?-Boc-N?-methyl-ethylene-diamine.To the solution of t-Bu-(PEG)3-amine (1 .01 g , 3.64 mmol) in 20 ml of methanol, (N-methyl)-N-Boc acetaldehyde(0.63 g, 3.64 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (0.412g, 10.9 mmol) was added to the mixture at 0C, and the resultant mixture was stirred at 0 C for 1 hour and 1 hour at room temperature. The reaction was quenched by adding 5 ml of water. After removal of solvent, 5 ml of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4, and the product was purified by flash silica chromatography using heptane/ethyl acetate to methylene chloride/methanol to give a yield of 72% (1.14 g). ?H NMR (300 MHz, CD2C12) oe ppm: 3.68 (t, 2H, OCH2), 3.56-3.60 (br, 1OH, CH2), 3.53 (t, 2H, OCH2), 3.29 (t, 2H, CH2), 2.85 (s, 3H, NCH3), 2.7-2.8 (m, 4H, NCH2), 2.47 (t, 2H, COCH2), 1.44 (s, 18H, CH3); MS-ESI (mle):435.5 [M+H].

Reference： [1]Patent: WO2015/116867,2015,A1 .Location in patent: Paragraph 00229

13
[ 756525-95-8 ]
[ 123387-72-4 ]
N-[(PEG)2-COO-t-Bu]-N‘-Boc-N’-methyl-ethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.6%		[00233j Synthesis of N- [(PEG)2-COO-t-Buj -N ?-Boc-N?-methyl-ethylenediamine. To the solution of N-(PEG)2C00-t-Bu-amine (1 .08g , 4.62 mmol) in 50 ml of methanol, (N-methyl)-NBoc acetaldehyde (0.8 g, 4.62 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (0.524, 13.9 mmol) was added to the mixture at 0C, and the resultant mixture was stirred at 0C for 1 hour and 1 hour at room temperature. The reaction was quenched by adding 5 ml of water. After removal of solvent, 5 ml of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4, and the product was purified by flash silica chromatography using heptane/ethyl acetate to methylene chloride/methanol to give a yield of 77.6% (1.40 g). ?H NMR (300 MHz, CD2C12) oe ppm: 3.67 (t, 2H, OCH2), 3.56-3.60 (br, 6H, OCH2), 3.29 (t, 2H, CH2), 2.85 (s, 3H, NCH3), 2.7-2.8 (m, 4H, NCH2), 2.46 (t, 2H, COCH2), 1.45 (s, 18H, CH3); MS-ESI (mle): 391.4 [M+H].

Reference： [1]Patent: WO2015/116867,2015,A1 .Location in patent: Paragraph 00233

14
[ 50479-22-6 ]
[ 123387-72-4 ]
N-[(CH2)3-COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.23 g	Stage #1: tert-butyl 4-aminobutanoate; O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate In methanol at 20℃; for 3h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h;	9 Synthesis of N- [(CH2)3-COO-t-Buj -N’-Boc-N’-methyl-ethylenediamine [00258j Synthesis of N- [(CH2)3-COO-t-Buj -N’-Boc-N’-methyl-ethylenediamine. To the solution of tert-butyl 4-aminobutanoate (1. 06g, 6.66 mmol) in 50 ml of methanol, (N-methyl)-NBOC acetaldehyde (1 .15 g, 6.66 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (0.755 g, 19.97 mmol) was added to the mixture at 0°C, and the resultant mixture was stirred at 0°C for 1 hour and at room temperature for 1 hour. The reaction was quenched by adding 5 ml of water. After removal of solvent, 5 ml of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4, and the solvent was removed. The product was purified by flash column chromatography using heptane/ethyl acetate followed by methylene chloride/methanol to give a yield of 105 % (2.23 g).

Reference： [1]Current Patent Assignee: PROMEGA CORP - WO2015/116867, 2015, A1 Location in patent: Paragraph 00258

15
[ 123387-72-4 ]
[ 5514-98-7 ]
N-[(CH2)5-COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate; 6-aminohexanoic acid tert-butyl ester In methanol at 20℃; for 3h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h;	10 Synthesis of N- [(CH2)5-COO-t-Buj -N’-Boc-N’-methyl-ethylenediamine [00274j Synthesis of N- [(CH2)s-COO-t-Buj -N’-Boc-N’-methyl-ethylenediamine. To the solution of tert-butyl 6-aminohexanoate (3.41g, 18.21 mmol) in 80 mL of methanol, (Nmethyl)-N-BOC acetaldehyde(3.15 g, 18.21 mmol) was added. The mixture was stirred at room temperature for 3 hours. NaBH4 (2.07 g, 54.62 mmol) was added to the mixture at 0°C, and the resultant mixture was stirred at 0°C for 1 hour and at room temperature for 1 hour. The reaction was quenched by adding 10 mL of water. After removal of solvent, 30 mL of water was added, and the mixture was extracted three times with methylene chloride. The combined organic layer was dried over Na2SO4 and dried down. The product was purified by flash column chromatography using heptane/ethyl acetate followed by methylene chloride/methanol.

Reference： [1]Current Patent Assignee: PROMEGA CORP - WO2015/116867, 2015, A1 Location in patent: Paragraph 00274

16
[ 13603-25-3 ]
[ 123387-72-4 ]
C₂₀H₃₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;

Reference： [1]Shen, Yudao; Szewczyk, Magdalena M.; Eram, Mohammad S.; Smil, David; Kaniskan, H. Ümit; Ferreira De Freitas, Renato; Senisterra, Guillermo; Li, Fengling; Schapira, Matthieu; Brown, Peter J.; Arrowsmith, Cheryl H.; Barsyte-Lovejoy, Dalia; Liu, Jing; Vedadi, Masoud; Jin, Jian [Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 9124 - 9139]

17
[ 123387-72-4 ]
[ 170304-83-3 ]
C₁₉H₃₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;

18
[ 3202-33-3 ]
[ 123387-72-4 ]
C₁₉H₃₀N₂O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9124 - 9139

19
[ 23056-29-3 ]
[ 123387-72-4 ]
C₁₉H₃₁N₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9124 - 9139

20
[ 1467-84-1 ]
[ 123387-72-4 ]
C₁₅H₃₀N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.5%		Compound 1 (100 g, 774.0 mmol) was dissolved in ethanol (1.5 L) N-tert-butoxycarbonyl-(methylamino)acetaldehyde (134.06 g, 774.0 mmol) was added, stirred for 10 minutes, Acetic acid (14.0 g, 232.2 mmol) was added and stirred at room temperature for 1 hour, After cooling to 0 C, sodium triacetoxyborohydride (328.1 g, 1548.0 mmol) Slowly rose to room temperature for 20 hours.The reaction mixture was concentrated, dissolved in dichloromethane (800 mL), stirred with water (800 mL), partitioned, and the aqueous phase was washed with dichloromethane (800 mL x 2). The resulting aqueous phase was adjusted to pH = 8-9 with sodium carbonate, extracted with dichloromethane (800 mL x 3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered,Concentrated to a brown oil 13 (210 g, 85% purity, 80.5% yield).

Reference： [1]Patent: CN105017219,2017,B .Location in patent: Paragraph 0064; 0065; 0066

21
[ 123387-72-4 ]
[ 75-64-9 ]
[ 89893-79-8 ]

Yield	Reaction Conditions	Operation in experiment
1.5 g	With sodium tris(acetoxy)borohydride; acetic acid In chloroform at 20℃;	16 First step: 4-(tetrahydro-2H-pyran-4-yl)piperazine-1-carboxylic acid tert-butyl ester General procedure: Piperazine-1-carboxylic acid tert-butyl ester (1.0 g, 5.37 mmol) was sequentially added to a 100 mL single-mouth bottle.Tetrahydro-4H-pyran-4-one (1.07g, 10.7mmol) and methanol (20mL), sodium cyanoborohydride (507mg, 8.06mmol) was added in portions, added, 0.5mL acetic acid was added, and the reaction was stirred at room temperature. 6-7h.The reaction was monitored by TLC. After completion of the reaction, the reaction was quenched with EtOAc EtOAc (EtOAc) The crude product was purified by column chromatography.Elution with DCM/MeOH = 20/1, product was collected and concentrated.1.5 g of a colorless oil were obtained.

Reference： [1]Current Patent Assignee: BEIJING ADAMADLE BIOTECHNOLOGY LIABILITY - CN108707139, 2018, A Location in patent: Paragraph 0253; 0255; 0259; 0260; 0261; 0262

22
[ 123387-72-4 ]
[ 145602-88-6 ]
[ 2415186-84-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate; methyl 3-amino-1-benzylpyrrolidine-3-carboxylate In methanol at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In methanol at 20℃; for 16h;	1 1) Synthesis of compound 3-2 Add compound 1 (630 mg, 2.69 mmol), compound 2 (698 mg, 4.03 mmol), methanol (15 mL) to a single-necked bottle (100 mL), react at room temperature for 1 hour, add sodium cyanoborohydride (253 mg, 4.03 mmol) ), The reaction was carried out at room temperature for 16 hours. The reaction solution was spin-dried and passed through a column with dichloromethane and methanol to obtain a yellow oil 3 (960 mg, yield 91%).

Reference： [1]Current Patent Assignee: SHANGHAI ENNOVABIO PHARMACEUTICALS; SHANGHAI YINUO PHARMACEUTICAL - CN111039947, 2020, A Location in patent: Paragraph 0163; 0165-0167

23
[ 100516-54-9 ]
[ 123387-72-4 ]
benzyl (3S,5S,6R)-3-((S)-2-((tert-butoxycarbonyl)(methyl)amino)-1-hydroxyethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate [ No CAS ]
benzyl (5S,6R)-3-(2-((tert-butoxycarbonyl)(methyl)amino)-1-hydroxyethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		General procedure: A solution of diphenyloxazinone (S,R)-4 (11.00g, 28.4mmol) in anhydrous DCM (300mL) was cooled to -5C (dry ice/acetone bath) under argon atmosphere and Bu2BOTf (1M solution in DCM, 56.8mL, 56.8mmol) over 15min was added, followed by Et3N (8.62g, 85.2mmol). The yellowish solution was stirred for 15min at -5C, then it was cooled to -78C and a solution of aldehyde 3a (8.85g, 51.1mmol) in anhydrous DCM (40mL) was added over 30min. After stirring at -78C for 1h the reaction was quenched by addition of phosphate buffer (pH 7) (100mL) at-78C. After warming to room temperature layers were separated and the aqueous layer was extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and volatiles were evaporated to afford crude 6a as 85:15 mixture of diastereomers. The crude oily 6a was mixed with EtOAc (100mL) and hexane (300mL), the obtained white suspension was stirred overnight and filtered. The precipitate (16g) was suspendedin EtOAc (100mL), stirred for 1h, filtered, and dried in vacuo to give desired compound (3S,5S,6R)-6a (9.04g, 56%) as a white solid (99% de). [alpha]21D [alpha]D21 +25.9 (c 1.16, MeOH). 1H NMR (400MHz, DMSO-d6) delta: (2:1 rotamer mixture) 7.43 - 7.06 (m, 10H), 7.03-6.95 (m, 2H), 6.70 - 6.53 (m, 4H), 6.51-6.48 (m, 1H), 6.00-5.91 (m, 1H), 5.29 (d, J=3.0Hz, 0.67H), 5.23 (d, J=3.0Hz, 0.33H), 5.14 - 5.05 (m, 1.66H), 5.02 (d, J=13.1Hz, 0.67H), 4.88 (d, J=13.1Hz, 0.67H), 4.06 - 3.97 (m, 1H), 3.85-3.68 (m, 1H), 1.39 (s, 9H), 1.28 (d, J=6.6Hz, 2H), 1.10 (d, J=6.6, 1H). 13C NMR (DMSO-d6) delta: 167.1, 167.0, 155.3, 153.8, 153.2, 136.7, 136.2, 136.1, 136.0, 134.9, 134.8, 128.3, 128.2, 128.1, 128.0, 127.7, 127.5, 127.4, 127.3, 127.2, 126.5, 126.1, 126.1, 78.3, 78.1, 77.5, 76.3, 75.4, 67.2, 66.4, 60.2, 60.0, 59.6, 48.9, 28.3, 18.0. HRMS (ESI) m/z: Calculated for C32H36N2NaO7 [M+Na]+ 583.2415, found 583.2416.

Reference： [1]Bioorganic and Medicinal Chemistry,2020,vol. 28

24
[ 192057-60-6 ]
[ 123387-72-4 ]
C₂₈H₃₅N₂O₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In 1,2-dichloro-ethane

Reference： [1]Quan, Xu; Kerdphon, Sutthichat; Peters, Bram B. C.; Rujirawanich, Janjira; Krajangsri, Suppachai; Jongcharoenkamol, Jira; Andersson, Pher G. [Chemistry - A European Journal, 2020, vol. 26, # 58, p. 13311 - 13316]

25
[ 123387-72-4 ]
[ 515160-72-2 ]
tert-butyl (2-{4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl}ethyl)methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium tris(acetoxy)borohydride; acetic acid In methanol at 20℃; for 0.5h;	2.1 Step 1 : Preparation of fer/-butyl (2-{4-[4-(2-methoxyethoxy)phenyl]piperazin- 1- yl } ethyl)methylcarbamate Acetic acid (0.18 mL) and /ert-butyl methyl(2-oxoethyl)carbamate (0.40 mL, 2.40 mmol) were added to a suspension of l-[4-(2-methoxyethoxy)phenyl]piperazine (0.51 g, 2.18 mmol) in methanol (7 mL). The resulting solution was treated with sodium triacetoxyborohydride (0.69 g, 3.68 mmol) and stirred at room temperature (rt) for 30 minutes. Water was added and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and washed with 1 M sodium carbonate (50 mL). The organic layer was dried over anhydrous magnesium sulfate, was filtered and the solvent was removed under reduced pressure. The residue was first purified by reverse phase.chromatography (5-100% water/ acetonitrile in 10 mM ammonium hydroxide/ water) and then by flash chromatography (3-10% methanol in dichloromethane) to afford /cvV-butyl (2-{4-[4-(2- methoxyethoxy)phenyl]piperazin-l-yl}ethyl)methylcarbamate (364 mg, 45% yield). 'H NMR (500 MHz, Chloroform -if) d 6.89 (m, 4H), 4.09 (dd, J = 5.5, 4.0 Hz, 2H), 3.75 (dd, J = 5.5, 4.0 Hz, 2H), 3.46 (s, 3H), 3.42 (m, 2H), 3.11 (t, J= 4.8 Hz, 4H), 2.91 (s, 3H), 2.68 (bs, 4H), 2.56 (bs, 2H), 1.48 (s, 9H). MS (El) for C21H35N3O4 : 394 (MH+).

Reference： [1]Current Patent Assignee: NEKTAR THERAPEUTICS - WO2020/227156, 2020, A1 Location in patent: Paragraph 00115-00117

26
[ 1001264-89-6 ]
[ 123387-72-4 ]
[ 2456378-89-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: (2S)-2-(4-chlorophenyl)-1-[4-[(5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-yiamino)propan-1-one; O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate In 1,2-dichloro-ethane at 20℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;

Reference： [1]Yamazoe, Sayumi; Tom, Jeffrey; Fu, Yue; Wu, Wenqiong; Zeng, Liang; Sun, Changlei; Liu, Qi; Lin, Jie; Lin, Kui; Fairbrother, Wayne J.; Staben, Steven T. [Journal of Medicinal Chemistry, 2020, vol. 63, # 6, p. 2807 - 2813]

27
[ 123387-72-4 ]
[ 171722-92-2 ]
C₂₆H₃₅N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1.5h;	1 Example 1 Synthesis of Compound 3 Combine piperidin-4-yl[1,1-biphenyl]-2-carbamate (5.04g, 17.0mmol) and NaHB(OAc)3 (7.21g, 34.0mmol)Sequentially add tert-butyl methyl(2-oxoethyl)carbamate(3.24g, 18.7mmol) containing the productIn a 100 ml flask in DCM (60 ml),The reaction solution was stirred at room temperature for 1.5 hours, and then 1N HCl (20 mL) was added and stirred vigorously.After standing, there are three layers, the water layer is separated and discarded.The organic layer was washed with 1N NaOH (20 mL) and saturated brine (20 mL), and dried with anhydrous magnesium sulfate.Filter and remove the solvent under reduced pressure to obtain a pale yellow oily liquid,The oil was purified by a fast adsorption column to obtain the target product 3 (7.63 g, yield 98%, HPLC purity 99%).

Reference： [1]Current Patent Assignee: SHANGHAI GUSEN PHARMACEUTICAL - CN112830890, 2021, A Location in patent: Paragraph 0050-0054

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tert-Butyl ethyl(2-hydroxyethyl)carbamate

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 123387-72-4 ] {[proInfo.proName]}

Quality Control of [ 123387-72-4 ]

Related Doc. of [ 123387-72-4 ]

Product Details of [ 123387-72-4 ]

Calculated chemistry of [ 123387-72-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 123387-72-4 ]

Application In Synthesis of [ 123387-72-4 ]

[ 123387-72-4 ] Synthesis Path-Upstream 1~9

[ 123387-72-4 ] Synthesis Path-Downstream 1~27

Related Functional Groups of [ 123387-72-4 ]

Aliphatic Chain Hydrocarbons

Aldehydes

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 123387-72-4 ]