[ CAS No. 77385-90-1 ] {[proInfo.proName]}

Name: 77385-90-1|Ethyl 2-(dibenzylamino)acetate|97%
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SKU: A169975
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2D 3D

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Quality Control of [ 77385-90-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 77385-90-1 ]

Product Details of [ 77385-90-1 ]

CAS No. :	77385-90-1	MDL No. :	MFCD00796343
Formula :	C₁₈H₂₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AFMDCFOWHWNQBP-UHFFFAOYSA-N
M.W :	283.37	Pubchem ID :	3553452
Synonyms :		Chemical Name :	Ethyl 2-(dibenzylamino)acetate

Safety of [ 77385-90-1 ]

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

Application In Synthesis of [ 77385-90-1 ]

* 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 [ 77385-90-1 ]
Downstream synthetic route of [ 77385-90-1 ]

[ 77385-90-1 ] Synthesis Path-Upstream 1~8

1
[ 77385-90-1 ]
[ 17360-47-3 ]

Reference： [1] Chemistry - An Asian Journal, 2012, vol. 7, # 6, p. 1372 - 1382

2
[ 623-73-4 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With [2-(4-hydroxymethyl)phenyl-4,4-(dimethyloxazole)Ru(CH₃CN)₄]PF₆ In diethyl ether; water at 20℃; for 0.7 h;	General procedure: A solution of amine (0.3 mmol in 4.0 mL Et₂O) was added to a solution of Ru(II)-hm-pheox 3 ( 0.0075 mmol, 2.5 molpercent) in water ( 1.0 mL), then EDA (0.3 mmol, 1.0 equiv.) was injected and the biphasic reaction mixture was stirred at room temperature. At the end of reaction, the ether layer was removed by decantation and the water-soluble catalyst washed three times with ether (3 x 5.0 mL). The collected ether phase which contain the aminoester product was dried over anhydrous Na₂SO₄ and evaporated under reduced pressure. The products in most cases were pure enough and there is no need for further purification. The water phase which contain the catalyst was recycled several times. The 2-piperazinone product was purified by using column chromatography on silica gel (by using CH₃OH only as eluent).
97%	With porous-polymer-supported ruthenium(II)-phenyloxazoline complex catalyst In dichloromethane at 20℃; for 0.25 h; Inert atmosphere	General procedure: A definite amount of polymer-supported ruthenium(II)-pheox complex cat. A was evacuated and backfilled with argon. The reaction flask was charged with (0.3 mmol) of amines dissolved in CH2Cl2 (3 mL) by injection through the side arm of the flask and the reaction flask was cooled in ice bath. Ethyldiazoacetate (0.035mL, 0.33 mmol) was slowly inserted and the reaction was stirred for 15 min at room temperature. The reaction product was isolated by centrifugation and the catalyst was separated by washing with acetonitrile and hexane respectively and dried under vacuum to be ready for the next use. The product in the filtrate was concentrated to afford the desired product in a pure form without further purification.
94%	With 1-methylimidazolium tetrafluoroborate In neat (no solvent) at 20℃; for 2 h;	General procedure: To a mixture of amine (2 mmol) and ethyl diazoacetate (see Table 1 for equivalents), [Hmim][BF4] (10 mol percent) was added. The mixture was stirred at room temperature until the completion of the reaction, as indicated by TLC. Next, H2O and CH2Cl2 were added. The mixture was decanted, the products being soluble in CH2Cl2. The ionic liquid being soluble in H2O was isolated after drying under vacuum and was reused in subsequent reactions.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 51, p. 4750 - 4754
[2] Asian Journal of Chemistry, 2017, vol. 29, # 2, p. 349 - 352
[3] Tetrahedron Letters, 2014, vol. 55, # 40, p. 5417 - 5419
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5351 - 5354
[5] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4467 - 4469

3
[ 105-36-2 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Yield	Reaction Conditions	Operation in experiment
97.3%	at 25℃; for 16 h;	Dibenzylamine (VI-1) (4.7 g, 23.9 mmol) was dissolved in dichloromethane (10 ml), ethyl bromoacetate (V-1) (2.0 g, 12 mmol) was added with stirring at 25 ° C, a white solid precipitates. Continue to stir about 16h, TLC monitoring reaction is completed, filtered, the filter cake was washed with dichloromethane, the filtrate was concentrated under reduced pressure to give a crude solid, recrystallization from petroleum ether / ethyl acetate (100: 1) gave 3.3 g of a white solid, yield 97.3percent.
67%	for 12 h; Reflux; Inert atmosphere	Exam le 9To a solution of dibenzylamine 63 (13.8 mL, 71 .9 mmol, 1 .1 equiv) in absolute ethanol (50 mL), ethyl bromoacetate (7.25 mL, 65.4 mmol) is added. The reaction mixture is refluxed for 12 h under argon. After evaporation under vaccum of most of the ethanol, 1 N sodium hydroxide (100 mL) and dichloromethane (700 mL) are added, and the phases separated. The organic layer is washed with water (100 mL), brine (100 mL) and dried (anhydrous Na₂SO₄). The crude product is crystallized from ethanol/water to give 64 (12.50g, 67percent yield) as white needle solid.

Reference： [1] Patent: CN106432330, 2017, A, . Location in patent: Paragraph 0190; 0191; 0192; 0193
[2] Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 2, p. 46 - 52
[3] Journal of the American Chemical Society, 1995, vol. 117, # 29, p. 7606 - 7610
[4] Patent: WO2012/31298, 2012, A2, . Location in patent: Page/Page column 70
[5] Patent: WO2006/28545, 2006, A2, . Location in patent: Page/Page column 159

4
[ 105-39-5 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	at 140℃; for 0.333333 h; Microwave irradiation	To a stirred solution of ethyl chloroacetate (1.0 g, 8.16 mmol) in EtOH (5.0 mL), dibenzylamine (2.09 g, 10.6 mmol) was added and the mixture heated at 140 °C in a microwave reactor for 20 min. After evaporation of the solvent, the crude was dissolved in CC1₂ and washed with a l.O M KOH solution and brine, then dried over Na₂S0₄, filtered, and concentrated in vacuo to give a crude product, as an oil. Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (98:2), gave the title compound (1.85 g, 80percent), as a white solid. MS (ESI) m/z: 284 [M-H]⁺ [¹HNMR as previously reported in literature: Synthesis, 1985, 9, 850-855].
80%	at 140℃; for 0.333333 h; Microwave irradiation	Step 1. Preparation of ethyl 2-(dibenzylamino)-acetate To a stirred solution of ethyl chloroacetate (1.0 g, 8.16 mmol) in EtOH (5.0 mL), dibenzylamine (2.09 g, 10.6 mmol) was added and the mixture heated at 140° C. in a microwave reactor for 20 min. After evaporation of the solvent, the crude was dissolved in CH₂Cl₂ and washed with a 1.0 M KOH solution and brine, then dried over Na₂SO₄, filtered, and concentrated in vacuo to give a crude product, as an oil. Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (98:2), gave the title compound (1.85 g, 80percent), as a white solid. MS (ESI) m/z: 284 [M-H]⁺[¹H NMR as previously reported in literature: Synthesis, 1985, 9, 850-855].

Reference： [1] Patent: WO2013/78430, 2013, A1, . Location in patent: Paragraph 0366
[2] ChemMedChem, 2014, vol. 9, # 2, p. 323 - 336
[3] Patent: US9353075, 2016, B2, . Location in patent: Page/Page column 126; 127
[4] Synthesis, 1985, vol. NO. 9, p. 850 - 855
[5] Journal of Organic Chemistry, 1951, vol. 16, p. 225,227
[6] Journal of Fluorine Chemistry, 2008, vol. 129, # 6, p. 510 - 514

5
[ 100-44-7 ]
[ 459-73-4 ]
[ 77385-90-1 ]

Yield	Reaction Conditions	Operation in experiment
96.03%	With triethylamine In dichloromethane at 25℃;	Glycine ethyl ester (10.3 g, 0.1 mol) was dissolved in dichloromethane (50 ml)Triethylamine (20.2 g, 0.2 mol) was added at 25 ° C,Benzyl chloride (25.32 g, 0.2 mol) was added with stirring,A white solid precipitates.Continue to stir,TLC monitoring reaction is completed,filter,The filter cake was washed with dichloromethane (20 ml)The combined filtrates were washed with water (100 ml)The organic layer was dried over anhydrous sodium sulfate,filter,Concentrated to give a solid,Recrystallization from petroleum ether / ethyl acetate (100: 1) gave 27.21 g of a white solid,The yield was 96.03percent.

Reference： [1] Patent: CN106432330, 2017, A, . Location in patent: Paragraph 0228; 0229; 0230

6
[ 18295-66-4 ]
[ 52742-32-2 ]
[ 77385-90-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 47, p. 11827 - 11831[2] Angewandte Chemie, 2012, vol. 124, # 47, p. 11997 - 12001

7
[ 24824-93-9 ]
[ 541-41-3 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 33, p. 7892 - 7901

8
[ 77385-90-1 ]
[ 623-33-6 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5671 - 5674

[ 77385-90-1 ] Synthesis Path-Downstream 1~88

1
[ 50-00-0 ]
[ 77385-90-1 ]
[ 134936-17-7 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

2
[ 18871-63-1 ]
[ 77385-90-1 ]
[ 125261-03-2 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

3
[ 623-43-8 ]
[ 77385-90-1 ]
[ 129397-17-7 ]

Reference： [1]Chemistry Letters,1990,p. 377 - 380

4
[ 383-63-1 ]
[ 77385-90-1 ]
[ 102608-34-4 ]

Reference： [1]Synthesis,1985,vol. NO. 9,p. 850 - 855

5
[ 1749-03-7 ]
[ 77385-90-1 ]
(3R,4S)-4-(4-Chloro-phenyl)-3-dibenzylamino-1-(4-methoxy-phenyl)-azetidin-2-one [ No CAS ]
(3S,4S)-4-(4-Chloro-phenyl)-3-dibenzylamino-1-(4-methoxy-phenyl)-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[2]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

6
[ 80542-40-1 ]
[ 77385-90-1 ]
(3R,4S)-3-Dibenzylamino-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one [ No CAS ]
(3S,4S)-3-Dibenzylamino-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[2]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

7
[ 77385-90-1 ]
[ 120419-97-8 ]
[ 134905-56-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 5147 - 5158

8
[ 77385-90-1 ]
[ 120419-97-8 ]
[ 134905-56-9 ]
[ 134905-56-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 5147 - 5158

9
[ 77385-90-1 ]
[ 76964-28-8 ]
[ 125261-04-3 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

10
[ 77385-90-1 ]
[ 69282-70-8 ]
[ 125261-06-5 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

11
[ 77385-90-1 ]
[ 95456-11-4 ]
[ 125261-07-6 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

12
[ 77385-90-1 ]
[ 95456-13-6 ]
[ 125261-09-8 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

13
[ 77385-90-1 ]
[ 72134-60-2 ]
[ 125261-12-3 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

14
[ 77385-90-1 ]
[ 125261-01-0 ]
[ 125261-10-1 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

16
[ 77385-90-1 ]
[ 125261-00-9 ]
[ 125261-05-4 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

17
[ 77385-90-1 ]
[ 125261-02-1 ]
[ 125261-11-2 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 763 - 768

18
[ 77385-90-1 ]
[ 90696-41-6 ]
(3S,4S)-3-Dibenzylamino-4-ethynyl-1-(4-methoxy-phenyl)-azetidin-2-one [ No CAS ]
(3R*,4S*)-3-(dibenzylamino)-4-ethynyl-1-(4-methoxyphenyl)azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

19
[ 77385-90-1 ]
[ 90696-41-6 ]
(3S,4S)-3-Dibenzylamino-4-ethynyl-1-(4-methoxy-phenyl)-azetidin-2-one [ No CAS ]
(3R*,4S*)-3-(dibenzylamino)-4-ethynyl-1-(4-methoxyphenyl)azetidin-2-one [ No CAS ]
(3R,4S)-3-Dibenzylamino-1-(4-methoxy-phenyl)-4-trimethylsilanylethynyl-azetidin-2-one [ No CAS ]
(3S,4S)-3-Dibenzylamino-1-(4-methoxy-phenyl)-4-trimethylsilanylethynyl-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

20
[ 77385-90-1 ]
[ 114070-41-6 ]
(3R,4S)-4-[(tert-Butyl-dimethyl-silanyl)-ethynyl]-3-dibenzylamino-1-(4-methoxy-phenyl)-azetidin-2-one [ No CAS ]
(3S,4S)-4-[(tert-Butyl-dimethyl-silanyl)-ethynyl]-3-dibenzylamino-1-(4-methoxy-phenyl)-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[2]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

21
[ 77385-90-1 ]
[ 80326-96-1 ]
[ 80326-97-2 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 892 - 893

22
[ 77385-90-1 ]
[ 1485-70-7 ]
[ 80326-96-1 ]
[ 80326-97-2 ]
[ 780-25-6 ]
[ 64805-08-9 ]
[ 103-49-1 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 892 - 893

23
[ 77385-90-1 ]
[ 538-51-2 ]
(3R,4S)-3-Dibenzylamino-1,4-diphenyl-azetidin-2-one [ No CAS ]
(3S,4S)-3-Dibenzylamino-1,4-diphenyl-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[2]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[3]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

24
[ 77385-90-1 ]
[ 783-08-4 ]
(3R,4S)-3-Dibenzylamino-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one [ No CAS ]
(3S,4S)-3-Dibenzylamino-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[2]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

25
[ 77385-90-1 ]
[ 100-52-7 ]
[ 134936-19-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

26
[ 77385-90-1 ]
[ 123-11-5 ]
[ 134936-20-2 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

27
[ 77385-90-1 ]
[ 104-94-9 ]
[ 433-27-2 ]
[ 99333-36-5 ]

Reference： [1]Synthesis,1985,vol. NO. 6-7,p. 609 - 611

28
[ 77385-90-1 ]
[ 75-07-0 ]
[ 134936-18-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

29
[ 105-36-2 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Yield	Reaction Conditions	Operation in experiment
97.3%	In dichloromethane; at 25℃; for 16h;	Dibenzylamine (VI-1) (4.7 g, 23.9 mmol) was dissolved in dichloromethane (10 ml), ethyl bromoacetate (V-1) (2.0 g, 12 mmol) was added with stirring at 25 C, a white solid precipitates. Continue to stir about 16h, TLC monitoring reaction is completed, filtered, the filter cake was washed with dichloromethane, the filtrate was concentrated under reduced pressure to give a crude solid, recrystallization from petroleum ether / ethyl acetate (100: 1) gave 3.3 g of a white solid, yield 97.3%.
67%	In ethanol; for 12h;Reflux; Inert atmosphere;	Exam le 9To a solution of dibenzylamine 63 (13.8 mL, 71 .9 mmol, 1 .1 equiv) in absolute ethanol (50 mL), ethyl bromoacetate (7.25 mL, 65.4 mmol) is added. The reaction mixture is refluxed for 12 h under argon. After evaporation under vaccum of most of the ethanol, 1 N sodium hydroxide (100 mL) and dichloromethane (700 mL) are added, and the phases separated. The organic layer is washed with water (100 mL), brine (100 mL) and dried (anhydrous Na2SO4). The crude product is crystallized from ethanol/water to give 64 (12.50g, 67% yield) as white needle solid.
	With triethylamine; In tetrahydrofuran;Heating / reflux;	Ethyl bromoacetate (19.52 mL, 176 mol) was added in a single portion to a chilled (0 C) solution of dibenzylamine (33.84 mL, 176 mmol) and triethylamine (27 mL, 193.6 mmol) in THF. The reaction mixture was stirred overnight at ambient temperature. Additional triethylamine (30 mL) and THF (100 mL) were added and the reaction mixture was heated at 50 0C for 1.5 hours. Additional ethyl bromoacetate (13 mL) was added and the reaction mixture was heated for 1 hour and then stirred at ambient temperature overnight. About half of the THF was removed under reduced pressure. The mixture was diluted with water (300 mL) and then extracted with ethyl acetate (2 x 400 mL). The combined extracts were washed sequentially with water and with brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography (700 g of silica gel, eluting with 20% ethyl acetate in hexanes) to provide 37.12 g of ethyl dibenzylaminoacetate as a colorless oil

Reference： [1]Patent: CN106432330,2017,A .Location in patent: Paragraph 0190; 0191; 0192; 0193
[2]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52
[3]Journal of the American Chemical Society,1995,vol. 117,p. 7606 - 7610
[4]Patent: WO2012/31298,2012,A2 .Location in patent: Page/Page column 70
[5]Patent: WO2006/28545,2006,A2 .Location in patent: Page/Page column 159

30
[ 77385-90-1 ]
[ 622-29-7 ]
[ 106501-85-3 ]
[ 106501-85-3 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 5147 - 5158

31
[ 77385-90-1 ]
[ 2362-79-0 ]
(3R,4S)-4-(4-Chloro-phenyl)-3-dibenzylamino-1-phenyl-azetidin-2-one [ No CAS ]
(3S,4S)-4-(4-Chloro-phenyl)-3-dibenzylamino-1-phenyl-azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532
[2]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

32
[ 77385-90-1 ]
[ 67-64-1 ]
[ 78758-94-8 ]

Yield	Reaction Conditions	Operation in experiment
54.8%		Diisopropylamine (56.0 g, 0.55 mol, 1.25 eq.) was dissolved in THF, cooled to -78C, n-butyl lithium (212 mL, 0.53 mol, 1.2 eq.) was added dropwise, and after the addition was completed, the reaction was carried out for 30 min. The prepared LDA solution was used as needed. Compound II-1 (125.0 g, 0.44 mol, 1.0 eq.) was dissolved in THF (2 L), and the above-mentioned LDA solution was added dropwise at -78C. After the addition was completed, the reaction was carried out for 30 min. Acetone (31.0 g, 0.53 mol, 1.2 eq.) was added dropwise, and the reaction was carried out for 2 h. The mixture was poured into a saturated ammonium chloride solution (1 L), and the layers were separated. The organic phase was dried and concentrated, then n-heptane (100 mL) was added, and the solid was separated by stirring in an ice water bath, filtered, and dried to give a white solid, 81.0 g, yield. : 54.8%.
52%		a) 2-Dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester; A solution of 11.3 g (40.0 mmol) dibenzylamino-acetic acid ethyl ester in 107 ml tetrahydrofuran and 107 ml toluene was stirred at -70 C. with 22 ml (44 mmol) lithium diisopropylamide (2M in heptane) for 30 minutes. 3.40 ml (46 mmol) acetone were added and stirring was continued overnight. The mixture was allowed to warm to room temprature, aqueous ammonium chloride solution was added. Extraction with diethylether and chromatography on silicagel with diethylether/heptane 1/2 yielded 7.16 g (52%) 2-dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester, MS m/e (%): 342.3 (M+H+, 100).

Reference： [1]Patent: CN109988126,2019,A .Location in patent: Paragraph 0075-0079
[2]Patent: US2006/122168,2006,A1 .Location in patent: Page/Page column 43
[3]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

33
[ 77385-90-1 ]
[ 109-94-4 ]
[ 134936-21-3 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

34
[ 24824-93-9 ]
[ 541-41-3 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 7892 - 7901

35
C₁₁H₂₅N₃S₂Si₂ [ No CAS ]
[ 77385-90-1 ]
dibenzylamino-(4-propylsulfanyl-[1,2,5]thiadiazol-3-yl)-acetic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 8285 - 8288

36
[ 77385-90-1 ]
cyclopropylmagnesium chloride [ No CAS ]
[ 960248-08-2 ]

Yield	Reaction Conditions	Operation in experiment
26%		Example 43a; 1,1-Dicyclopropyl-2-dibenzylamino-ethanol; To 20 ml of a 0.5 M (0.010 mol) solution of cyclopropylmagnesium chloride in tetrahydrofuran was a solution of 1.00 g (0.004 mol) dibenzylamino-acetic acid ethyl ester in 10 ml tetrahydrofuran and the mixture was allowed to stir at room temperature for 18 h. The reaction mixture was partitioned between 10% aqueous ammonium chloride and ethyl acetate the phases were separated and the organic phase was purified by chromatography on silca gel with heptane:ethyl acetate=9:1 to 4:1 to yield 0.29 g (26% Th) of the title compound as light yellow oil. MS (ISP) (M+H+)=322.3.

Reference： [1]Patent: US2007/293509,2007,A1 .Location in patent: Page/Page column 22-23

37
[ 77385-90-1 ]
(2S,3R)-3-Amino-2-dibenzylamino-pent-4-enoic acid methoxy-methyl-amide [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

38
[ 77385-90-1 ]
(-)-1-[(R)-3-(dibenzylamino)-4-oxocyclopent-2-enyl]-1H-pyrrole-2-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

39
[ 77385-90-1 ]
[ 847033-97-0 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

40
[ 77385-90-1 ]
[ 847034-03-1 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

41
[ 77385-90-1 ]
[ 847034-05-3 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

42
[ 77385-90-1 ]
[ 847034-02-0 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

43
[ 77385-90-1 ]
[ 847033-98-1 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

44
[ 77385-90-1 ]
[ 847034-01-9 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 621 - 623

45
[ 77385-90-1 ]
(2R,3S)-3-Amino-2-dibenzylamino-3-phenyl-propionic acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 2789 - 2792

46
[ 77385-90-1 ]
1-((benzylamino)methyl)cyclopropan-1-ol [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 1238 - 1243

47
[ 77385-90-1 ]
(Z)-(3R*,4S*)-4-<2-(t-butyldimethylsilyl)vinyl>-3-dibenzylamino-1-(4-methoxyphenyl)azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

48
[ 77385-90-1 ]
(E)-(3R*,4S*)-4-<2-(t-butyldimethylsilyl)vinyl>-3-dibenzylamino-1-(4-methoxyphenyl)azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

49
[ 77385-90-1 ]
(Z)-(3R*,4R*)-4-<2-(t-butyldimethylsilyl)vinyl>-3-dibenzylamino-1-(4-methoyphenyl)azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

50
[ 77385-90-1 ]
(E)-(3R*,4R*)-4-<2-(t-butyldimethylsilyl)vinyl>-3-dibenzylamino-1-(4-methoxyphenyl)azetidin-2-one [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 527 - 532

51
[ 77385-90-1 ]
[ 102608-35-5 ]

Reference： [1]Synthesis,1985,vol. NO. 9,p. 850 - 855

52
[ 77385-90-1 ]
[ 102608-35-5 ]

Reference： [1]Synthesis,1985,vol. NO. 9,p. 850 - 855

53
[ 77385-90-1 ]
[ 134936-23-5 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 46 - 52

54
[ 821-06-7 ]
[ 77385-90-1 ]
rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Method B Preparation of Racemic (lR, 2S)/ (1S, 2R) 1-amino-2-vinylcyclopropane carboxylic acid ethyl ester hydrochloride To a solution of potassium tert-butoxide (11 55 g, 102.9 mmol) in THF (450 mL) at -78 C was added the commercially available N, N dibenzyl imine of glycine ethyl ester (25.0 g, 93.53 mmol) in THF (112 mL) The reaction mixture was warmed to 0 C, stirred for 40 min, and was then cooled back to-78 C. To this solution was added trans-1, 4-dibromo-2-butene (20.0 g, 93.50 mmol), the mixture stirred for 1 h at 0 C and was cooled back to -78 C. Potassium tert-butoxide (11.55 g, 102.9 mmol) was added, the mixture immediately warmed to 0 C, and was stirred one more hour before concentrating in vacuo. The crude product was taken up in Et2O (530 mL), 1N aq. HCl solution (106 mL, 106 mmol) added and the resulting biphasic mixture stirred for 3.5 h at rt. The layers were separated and the aqueous layer was washed with Et2O (2x) and basified with a saturated aq. NaHC03 solution. The desired amine was extracted with Et20 (3x) and the combined organic extract was washed with brine, dried (MgS04), and concentrated in vacuo to obtain the free amine. This material was treated with a 4N HCl solution in dioxane (100 mL, 400 mmol) and concentrated to afford (lR, 2S)/(1S,2R)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester hydrochloride as a brown semisolid (5.3 g, 34% yield) identical to the material obtained from procedure A, except for the presence of a small unidentified aromatic impurity (8%).

Reference： [1]Patent: WO2005/46712,2005,A1 .Location in patent: Page/Page column 62

55
[ 77385-90-1 ]
[ 120419-97-8 ]
3-dibenzylamino-4-phenyl-2-azetidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;	Example II Synthesis of 3-dibenzylamino-4-phenyl-2-azetidinone 10 mmoles of n-butyllithium (6.67 ml of a 1.5 molar solution in hexane) was added to a stirred solution of diisopropylamine (1.40 ml; 10 mmoles) in 25 ml of tetrahydrofuran at 0C. After stirring for 15 minutes <strong>[77385-90-1]N,N-dibenzyl glycine ethyl ester</strong> (2.83 g; 10 mmoles) was added at 0C. The reaction mixture was stirred for another 15 minutes at room temperature and then N-(benzylidene)trimethylsilylamine was added. The mixture was stirred for 1 hour at room temperature and an additional 15 minutes at 50C. After cooling to room temperature the reaction mixture was quenched with 30 ml of a saturated aqueous ammonium chloride solution. The water layer was extracted with diethyl ether. The diethyl ether extract was dried with sodium sulphate and concentrated in vacuo to afford 3.11 g (91%) of the pure 2-azetidinone product as an off-white solid. The 1H NMR spectrum revealed that the product was a mixture of cis - and trans -isomers (cis : trans ratio 84:16). The pure cis product was obtained after recrystallization from diethyl ether as colourless crystals with the properties: m.p. 80C. 1H NMR (CDCl3): delta 7.43-7.35, 7.28-7.18 and 7.05-7.00 (mp, 5H, mp, 6H, mp, 4H, protons of the phenyl group), 6.52 (br. s, 1H, NH), 4.78 (db, 1H, J = 5.3 Hz, C H -C-Ph), 4.54 (ddb, 1H, J = 5.3 Hz and J = 1.84 Hz, C-C H -Ph), 3.67 (db, 2H, J = 13.6 Hz, CH2Ph), 3.51 (db, 2H, J = 13.6 Hz, CH2Ph). 13C NMR (CDCl3): delta 170.42 (C=O), 138.56, 137.40, 128.91, 128.52, 128.12, 127.79, 127.13 and 127.07 (carbon atoms of the phenyl groups), 73.69 (C H-C-Ph), 58.31 (C- C H-Ph), 55.53 (C H2Ph).

Reference： [1]Patent: EP442576,1991,A1

56
[ 77385-90-1 ]
[ 3375-31-3 ]
[Pd(O₂CCH₃)(C₆H₄CH₂N(CH₂C₆H₅)(CH₂CO₂C₂H₅))]2*1.5H₂O [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1995,vol. 73,p. 1164 - 1174

57
[ 352-24-9 ]
[ 77385-90-1 ]
C₂₀H₂₁F₂NO₃ [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2008,vol. 129,p. 510 - 514

58
[ 77385-90-1 ]
[ 372-31-6 ]
C₂₀H₂₀F₃NO₃ [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2008,vol. 129,p. 510 - 514

59
[ 623-73-4 ]
[ 103-49-1 ]
[ 77385-90-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With [2-(4-hydroxymethyl)phenyl-4,4-(dimethyloxazole)Ru(CH3CN)4]PF6; In diethyl ether; water; at 20℃; for 0.7h;	General procedure: A solution of amine (0.3 mmol in 4.0 mL Et2O) was added to a solution of Ru(II)-hm-pheox 3 ( 0.0075 mmol, 2.5 mol%) in water ( 1.0 mL), then EDA (0.3 mmol, 1.0 equiv.) was injected and the biphasic reaction mixture was stirred at room temperature. At the end of reaction, the ether layer was removed by decantation and the water-soluble catalyst washed three times with ether (3 x 5.0 mL). The collected ether phase which contain the aminoester product was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The products in most cases were pure enough and there is no need for further purification. The water phase which contain the catalyst was recycled several times. The 2-piperazinone product was purified by using column chromatography on silica gel (by using CH3OH only as eluent).
97%	With porous-polymer-supported ruthenium(II)-phenyloxazoline complex catalyst; In dichloromethane; at 20℃; for 0.25h;Inert atmosphere;	General procedure: A definite amount of polymer-supported ruthenium(II)-pheox complex cat. A was evacuated and backfilled with argon. The reaction flask was charged with (0.3 mmol) of amines dissolved in CH2Cl2 (3 mL) by injection through the side arm of the flask and the reaction flask was cooled in ice bath. Ethyldiazoacetate (0.035mL, 0.33 mmol) was slowly inserted and the reaction was stirred for 15 min at room temperature. The reaction product was isolated by centrifugation and the catalyst was separated by washing with acetonitrile and hexane respectively and dried under vacuum to be ready for the next use. The product in the filtrate was concentrated to afford the desired product in a pure form without further purification.
94%	With 1-methylimidazolium tetrafluoroborate; In neat (no solvent); at 20℃; for 2h;	General procedure: To a mixture of amine (2 mmol) and ethyl diazoacetate (see Table 1 for equivalents), [Hmim][BF4] (10 mol %) was added. The mixture was stirred at room temperature until the completion of the reaction, as indicated by TLC. Next, H2O and CH2Cl2 were added. The mixture was decanted, the products being soluble in CH2Cl2. The ionic liquid being soluble in H2O was isolated after drying under vacuum and was reused in subsequent reactions.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4750 - 4754
[2]Asian Journal of Chemistry,2017,vol. 29,p. 349 - 352
[3]Tetrahedron Letters,2014,vol. 55,p. 5417 - 5419
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 5351 - 5354
[5]Tetrahedron Letters,2009,vol. 50,p. 4467 - 4469

60
[ 77385-90-1 ]
[ 623-33-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5671 - 5674

61
C₁₁H₁₃NOS [ No CAS ]
[ 77385-90-1 ]
[ 1219366-56-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step 5-B:5eTo a solution of ethyl (dibenzylamino)acetate 5d (9.15 g, 32.3 mmol) in anhydrous THF (170 niL) at -78 0C is added IN LiHMDS in THF (32.3 mL, 32.3 mmol) dropwise. The mixture is stirred for 1 hr and then a solution of 5c in THF (10 mL) is added dropwise. The reaction mixture is stirred at -78 0C for 30 minutes, quenched by addition of sat. aq. NH4Cl and warmed to room temperature. The aqueous phase is extracted with EtOAc and the combined organic phases are washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue is chromatographed on Silica gel (gradient: EtO Ac/heptane; 0% to 40%) to afford 5e (3.11 g) as the major isomer. Found m/z ES+ = 491.

Reference： [1]Patent: WO2010/31750,2010,A1 .Location in patent: Page/Page column 50

62
[ 847034-00-8 ]
[ 77385-90-1 ]
[ 847033-99-2 ]

Yield	Reaction Conditions	Operation in experiment
73%		Example 2[0055] In a 25-mL, one-necked, round-bottomed flask equipped with a magnetic stirring bar, rubber septum, and argon balloon was placed 5 (3.3 g, 11.6 mmol), Et2O (8.0 mL). The solution was cooled to O0C. In a second 100-mL, one-necked, round-bottomed flask equipped with a magnetic stirring bar, rubber septum, and argon balloon was placed LDA (5.8 mL, 2.0 M in cyclohexane/heptane^enzene from Aldrich) and Et2O (30.0 mL). The solution of 5 was added via a double-end needle at -780C. The yellow-orange solution was stirred for 30 minutes at this temperature and sulfinimine (-)-6 (0.45Og, 2.33 mmol) in Et2O (6.0 mL) was added dropwise at - 780C. The solution was stirred at this temperature, monitored by TLC for completion (about 30 min), and quenched by addition of sat. aq. NH4Cl (10 mL). The solution mixture was warmed to room temperature (hereinafter referred to as "rt") and the aqueous phase was separated and extracted with EtOAc (3 X 10 mL). The combined organic phases were washed with brine (15 mL), dried (Na2SO4), and concentrated. Chromatography (5% and then 10% EtOAc/hexane) afforded 0.810 g (73%) of a yellow oil; [?]20D = -121.4 (c 1.7, CHCl3); IR (neat): 3229, 1734, 1465, 1094 cm"1; 1H NMR (CHCl3) ? 1.35 (t, J= 7.0 Hz, 3 H), 2.48 (s, 3 H), 3.17 (d, J= 10.5 Hz, 1 H), 3.30 (d, J= 13.0 Hz, 2 H), 3.95 (d, J= i3.0 Hz, 2 H), 4.27 (m, 2 H), 4.38 (dd, J= 7.5 Hz, J=10.5 Hz, 1 H), 5.15 (s, 1 H), 5.30 (m, 1 H), 5.45-5.57 (m, 2 H), 7.12-7.23 (m, 10 H), 7.32 (d, J = 8.0 Hz , 2 H), 7.56 (d, J = 8.0 Hz , 2 H); 13C NMR ? 14.8, 21.7, 53.4, 54.4, 60.8, 64.6, 122.0, 125.4, 127.5, 128.6, 129.6, 134.7, 138.2, 141.4, 143.2, 168.8 (one carbon miss due to the overlap in the aromatic region). HRMS calculated for C28H32N2O3SNa (M + Na): 499.2031. Found: 499.2041. The thus formed (5R,25,3i?)-(-)-Ethyl-2-(N,N-dibenzylamino)-3-N-(p- toluenesulfinyl)amino-pent-4-enoate (4) has the formula

Reference： [1]Patent: WO2006/55578,2006,A2 .Location in patent: Page/Page column 12 - 13; 3/5

63
[ 77385-90-1 ]
[ 106-95-6 ]
ethyl 2-(N,N-dibenzylamino)-4-pentenoate [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5128 - 5131

64
[ 454-31-9 ]
[ 77385-90-1 ]
C₂₀H₂₁F₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		To a solution of 64 (2.00g, 0.71 mmol) and ethyl fluoroacetate (15.53 mmol) in anhydrous tetrahydrofuran (15 mL), sodium hydride (50 % suspension in mineral oil) (1 .02 g, 25.42 mmol) is added. The reaction mixture is refluxed for 5 h under argon and then cooled to 0 C and treated with acetic acid (1 .42 mL, 26.10 mmol). Sodium borohydride (668 mg, 17.66 mmol) is then added and the suspension is stirred overnight (14 h) at room temperature. The result deep red solution is treated with 1 N hydrochloride acid to pH=5, stirred for 10 min, and then treated with sat. NaHCO3 (100 mL) to pH=9-10. The mixture is extracted with EtOAc (3x80 mL). The combined organic layers are washed with water (30 mL), brine (30 mL), and dried (anhydrous Na2SO4). The crude product is purified by CombiFlash (eluting with 0-10 % EtOAc in hexane) to obtain the 66 as a white solid.

Reference： [1]Patent: WO2012/31298,2012,A2 .Location in patent: Page/Page column 70; 72

65
[ 77385-90-1 ]
C₂₀H₂₃F₂NO₃ [ No CAS ]

Reference： [1]Patent: WO2012/31298,2012,A2

66
[ 120-57-0 ]
[ 77385-90-1 ]
ethyl 3-(benzo[1,3]dioxol-5-yl)-2-(dibenzylamino)-3-hydroxypropanoate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 1372 - 1382

67
[ 120-57-0 ]
[ 77385-90-1 ]
ethyl 3-acetoxy-3-(benzo[1,3]dioxol-5-yl)-2-(dibenzylamino)propanoate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 1372 - 1382

68
[ 77385-90-1 ]
[ 1381774-94-2 ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 1372 - 1382

69
[ 77385-90-1 ]
isopropyl 2-(dibenzylamino)-3-hydroxy-3-(4-methoxyphenyl)propanoate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 1372 - 1382

70
[ 77385-90-1 ]
[ 17360-47-3 ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 1372 - 1382

71
[ 77385-90-1 ]
[ 123-11-5 ]
ethyl 2-(dibenzylamino)-3-hydroxy-3-(4-methoxyphenyl)propanoate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 1372 - 1382

72
[ 18295-66-4 ]
[ 52742-32-2 ]
[ 77385-90-1 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 11827 - 11831
Angewandte Chemie,2012,vol. 124,p. 11997 - 12001

73
[ 77385-90-1 ]
[ 79-03-8 ]
[ 1439368-21-4 ]

Yield	Reaction Conditions	Operation in experiment
0.6 g		In a round bottomed flask, at -78 C, under argon atmosphere, a solution of DIP A (0.3 mL, 2.12 mmol) in dry THF (10 ml) was treated with ra-BuLi (2.5 M in -hexane, 0.776 mL, 1.94 mmol). After 30 min a solution of <strong>[77385-90-1]ethyl 2-(dibenzylamino)-acetate</strong> (0.5 g, 1.77 mmol) in dry THF (10 ml) was added dropwise via a cannula. After 15 min, propanoyl chloride (0.46 mL, 5.29 mmol) was added dropwise at -78 C and the mixture stirred for 10 min at rt. The reaction was then quenched with H20, and Et20 was subsequently added. The organic layer was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo to give a crude product, as an oil. Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (98:2) gave a pure compound (0.6 g), as a mixture of two tautomers (ketone:enol= ca. 85:15), as a colorless oil. MS (ESI) m/z: 340 [M-H]+; (ESI) m/z: 338 [M-H]-. 1H NMR (DMSO-d6) delta 0.90 (t, J= 7.24 Hz, 3H), 1.23 (t, J= 7.07 Hz, 3H), 2.53-2.61 (m, 1H), 2.69 (dq, J= 7.23, 18.13 Hz, 1H), 3.72-3.88 (m, 4H), 4.12-4.22 (m, 3H), 7.11-7.47 (m, 10H) (reported data refer to the major ketone tautomer).

Reference： [1]Patent: WO2013/78430,2013,A1 .Location in patent: Paragraph 0367
[2]ChemMedChem,2014,vol. 9,p. 323 - 336

74
[ 77385-90-1 ]
erythro-(2SR,3RS)-ethyl 2-(dibenzylamino)-3-hydroxy-pentanoate [ No CAS ]

Reference： [1]Patent: WO2013/78430,2013,A1
[2]ChemMedChem,2014,vol. 9,p. 323 - 336

75
[ 77385-90-1 ]
erythro-(2SR,3RS)-ethyl 2-(dibenzylamino)-3-hydroxy-4-methyl-pentanoate [ No CAS ]

Reference： [1]Patent: WO2013/78430,2013,A1
[2]ChemMedChem,2014,vol. 9,p. 323 - 336

76
[ 77385-90-1 ]
erythro-(2SR,3RS)-ethyl 2-(dibenzylamino)-3-hydroxy-4,4-dimethyl-pentanoate [ No CAS ]

Reference： [1]Patent: WO2013/78430,2013,A1
[2]ChemMedChem,2014,vol. 9,p. 323 - 336

77
[ 77385-90-1 ]
[ 3282-30-2 ]
[ 1439368-50-9 ]

Yield	Reaction Conditions	Operation in experiment
76%		In a round bottomed flask, at -78 C, under argon atmosphere, a solution of DIPA (0.29 mL, 2.12 mmol) in dry THF (10 ml) was treated with n-BuU (2.5 M in-hexane, 0.776 mL, 1.94 mmol). After 30 min a solution of <strong>[77385-90-1]ethyl 2-(dibenzylamino)-acetate</strong> [prepared as described in Example 47, step 1] (0.5 g, 1.77 mmol) in dry THF (10 mL) was added dropwise via cannula. After 15 min, trimethylacetyl chloride (0.53 mL, 3.53 mmol) was added dropwise at -78 C and the mixture stirred for 10 min at rt. The reaction was then quenched with H20, and Et20 was subsequently added. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product as an oil. Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (98:2) gave the title compound (0.492 g, 76%) as a colorless oil. MS (ESI) m/z: 368 [M-H]+; (ESI) m/z: 366 [M-H]- .1H NMR (DMSO-d6) delta 0.93 (s, 9H), 1.16 - 1.25 (m, 3H), 3.79 (d, J = 13.97 Hz, 2H), 3.98 (d, J = 13.96 Hz, 2H), 4.07 - 4.25 (m, 2H), 4.60 (s, 1H), 7.20 - 7.41 (m, 10H).

Reference： [1]Patent: WO2013/78430,2013,A1 .Location in patent: Paragraph 0399
[2]ChemMedChem,2014,vol. 9,p. 323 - 336

78
[ 77385-90-1 ]
2-(dibenzylamino)-2-(4-hydroxytetrahydro-2H-pyran-4-yl)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7772 - 7787

79
[ 77385-90-1 ]
2-(dibenzylamino)-2-(4-(2-nitrophenoxy)tetrahydro-2H-pyran-4-yl)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7772 - 7787

80
[ 77385-90-1 ]
2-(4-(2-aminophenoxy)tetrahydro-2H-pyran-4-yl)-2-(dibenzylamino)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7772 - 7787

81
[ 77385-90-1 ]
3-(dibenzylamino)-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]-oxazepine-2,4′-pyran]-4(5H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7772 - 7787

82
[ 29943-42-8 ]
[ 77385-90-1 ]
ethyl 2-(dibenzylamino)-2-(4-hydroxytetrahydro-2H-pyran-4-yl)acetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7772 - 7787

83
[ 77385-90-1 ]
[ 79-30-1 ]
[ 1439368-35-0 ]

Yield	Reaction Conditions	Operation in experiment
		In a round bottomed flask, at -78 C, under argon atmosphere, a solution of DIP A (1.6 ml, 9.3 mmol) in dry THF (40 ml) was treated with -BuLi (2.5 M in -hexane, 3.4 ml, 8.5 mmol). After 30 min a solution of <strong>[77385-90-1]ethyl 2-(dibenzylamino)-acetate</strong> [prepared as described in Example 47, step 1] (2.2 g, 7.8 mmol) in dry THF (40 ml) was added dropwise via cannula. After 15 min, 2-methyl-propanoyl chloride (2.4 mL, 23.3 mmol) was added dropwise at -78 C and the mixture stirred for 10 min at rt. The reaction was then quenched with H20, and Et20 was subsequently added. The organic layer was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo to give a crude product, as an oil.Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (98:2) gave a crude compound (3.2 g) as a mixture of two tautomers (ketone:enol= ca. 65:35), as a colorless oil, which was used without further purification in the following step. Ketone isomer. MS (ESI) m/z: 354 [M-H]+; (ESI) m/z: 352 [M-H]- 1H NMR (DMSO- d6) delta 0.86 (d, J= 6.73 Hz, 3H), 0.91 (d, J = 7.01 Hz, 3H), 1.22 (t, J = 7.1 1 Hz, 3H), 2.99 (hept, J= 6.90 Hz, 1H), 3.78 (d, J= 14.1 1 Hz, 2H), 3.84 (d, J= 14.13 Hz, 2H), 4.10 - 4.24 (m, 2H), 4.29 (s, 1H), 7.17 - 7.48 (m, 10H). Enol isomer. MS (ESI) m/z: 354 [M-H]+; (ESI) m/z: 352 [M-H]". NMR (DMSO-d6) delta 0.48 (s, 3H), 0.50 (s, 3H), 1.43 (t, J= 7.09 Hz, 3H), 3.16 - 3.28 (m, 1H), 3.90 (d, J= 12.66 Hz, 2H), 3.96 (d, J= 12.66 Hz, 2H), 4.38 (q, J= 7.08 Hz, 2H), 7.10 - 7.46 (m, 10H), 12.32 (s, 1H).

Reference： [1]Patent: WO2013/78430,2013,A1 .Location in patent: Paragraph 0366; 0382
[2]ChemMedChem,2014,vol. 9,p. 323 - 336

84
[ 77385-90-1 ]
[ 1562189-83-6 ]

Reference： [1]Patent: WO2014/23708,2014,A1

85
[ 77385-90-1 ]
[ 1562189-98-3 ]

Reference： [1]Patent: WO2014/23708,2014,A1

86
[ 77385-90-1 ]
[ 1562190-00-4 ]

Reference： [1]Patent: WO2014/23708,2014,A1

87
[ 77385-90-1 ]
[ 1562190-03-7 ]

Reference： [1]Patent: WO2014/23708,2014,A1

88
[ 77385-90-1 ]
[ 108-94-1 ]
[ 1562189-86-9 ]

Yield	Reaction Conditions	Operation in experiment
30%		Step 1 : Ethyl 2-(dibenzylamino)acetate (4.92 g, 17.4 mmol, Eq: 1.2) in THF (40 mL) was added to a solution of LDA in THF at -40 C. After 15 min. the mixture was cooled to -78 C and cyclohexanone (1.42 g, 1.5 mL, 14.5 mmol, Eq: 1.00) in THF (10 mL) was added. After 2 h, 10 mL of sat. NH4C1 was added and the mixture warmed to RT. After 2 h, the mixture was diluted with H20 and extracted with EtOAc. The combined extracts were washed with H20, dried over Na2S04 and concentrated. The residue was purified by flash chromatography to give 2-(dibenzylamino)-2-(l-hydroxycyclohexyl)acetate as a colorless oil (1.63 g, 30 %) MS m/z 382.1 (MH+)

Reference： [1]Patent: WO2014/23708,2014,A1 .Location in patent: Page/Page column 69

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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. 77385-90-1 ] {[proInfo.proName]}

Quality Control of [ 77385-90-1 ]

Related Doc. of [ 77385-90-1 ]

Product Details of [ 77385-90-1 ]

Safety of [ 77385-90-1 ]

Application In Synthesis of [ 77385-90-1 ]

[ 77385-90-1 ] Synthesis Path-Upstream 1~8

[ 77385-90-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 77385-90-1 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 77385-90-1 ]