[ CAS No. 84348-38-9 ] {[proInfo.proName]}

Name: 84348-38-9|(S)-1-(tert-Butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid|97%
Brand: Ambeed
SKU: A158563
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Quality Control of [ 84348-38-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 84348-38-9 ]

SDS Specification

Alternatived Products of [ 84348-38-9 ]

Product Details of [ 84348-38-9 ]

CAS No. :	84348-38-9	MDL No. :	MFCD01861787
Formula :	C₁₁H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ULLGRIBXGPATMA-QMMMGPOBSA-N
M.W :	227.26	Pubchem ID :	21727417
Synonyms :

Calculated chemistry of [ 84348-38-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.64
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.7
TPSA :	66.84 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) :	-6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	1.04
Log Po/w (WLOGP) :	1.26
Log Po/w (MLOGP) :	0.93
Log Po/w (SILICOS-IT) :	0.59
Consensus Log Po/w :	1.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.64
Solubility :	5.2 mg/ml ; 0.0229 mol/l
Class :	Very soluble
Log S (Ali) :	-2.03
Solubility :	2.1 mg/ml ; 0.00925 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.76
Solubility :	39.3 mg/ml ; 0.173 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.14

Safety of [ 84348-38-9 ]

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

Application In Synthesis of [ 84348-38-9 ]

* 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 [ 84348-38-9 ]
Downstream synthetic route of [ 84348-38-9 ]

[ 84348-38-9 ] Synthesis Path-Upstream 1~9

1
[ 1779-49-3 ]
[ 84348-37-8 ]
[ 84348-38-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 2 h; Stage #2: at 0 - 20℃;	Example 2. Preparation of (S)-l -(fert-butoxycarbonyl)-4-methylenepyrrolidine-2- carboxylic acidTo a mixture of methyltriphenylphosphonium bromide (236.4 g, 2.7 eq) in THF (1 L) was rapidly added potassium tert-butoxide (75.6 g, 2.75 eq) while maintaining the temperature around 0 °C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 hours, and re-cooled to 0 °C. (S)- l-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (56.2 g, 0.245 mol) was added portionwise to the reaction mixture while maintaining the temperature below 5 °C. Then, the reaction was allowed to warm to room temperature and stirred at room temperature overnight befroe being re-cooled to 0 °C and quenched by addition of saturated NaHC0₃ solution (500 mL) and water (200 mL). The mixture was evaporated. The aqueous layer was extracted with tert-butyl methyl ether (2 x 400 mL). The aqueous layer was filterd through a pad of celite and the filtrate was acidified with 6N HC1 (200 mL) and extracted with ethyl acetate (2 x 1L). The combined organic layers were washed with brine, dried (Na₂S0₄), filtered and evaporated to dryness. The residue was dissolved in ethyl acetate (0.7 L), extracted with 0.5 N NaOH (0.7 and 0.3 L). The aqueous layer was acidified with 6N HC1 (100 mL), extracted with ethyl acetate (1 L and 0.8 L). The combined organic layers were washed with brine, dried (Na₂S0₄), filtered and evaporated to dryness. The residue was dissolved in 50percent ethyl acetate in cyclohexane (150 mL), slowly evaporated to give a yellowish solid. It was filtered and dried to give the title compound (26 g). The filtrate was evaporated to give a yellowish solid, filtered and dried to provide the title compound (10 g). Total 36 g (65percent>) as a white solid. Also, the residue contained 18 g of the product as 80percent purity. 1H NMR (500 MHz, CDCls): 5.04-5.02 (m, 2H), 4.53 (dd, J= 8.4, 3.2 Hz, 0.5H), 4.42 (d, J= 9.3 Hz, 0.5H), 4.09-3.98 (m, 2H), 3.05-2.69 (m, 2H), 1.49 and 1.43 (2 s, 9H).
5.1 g	Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 2 h; Stage #2: at 20℃; for 0.5 h;	To a mixture of methyltriphenylphosphonium bromide (11.7 g, 32.7 mmol) in THF (150 mL) was rapidly added potassium tert-butoxide (3.67 g, 32.7 mmol) while maintaining the temperature around 0° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 hrs. The mixture was cooled to 0° C. and (S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (5 g, 21.8 mmol) was added in portions. The reaction was allowed to warm to room temperature and stirred at room temperature for 30 min. After quenching with addition of saturated aq.NaHCO₃solution, the mixture was washed with ether (2×50 mL). The aqueous was acidified with 2 N HCl to pH=2 and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried over anhydrous Na₂SO₄, filtered and evaporated under reduced pressure to give the title compound (5.1 g) as a yellow oil, which was without further purification for next step.

Reference： [1] Patent: WO2012/158861, 2012, A2, . Location in patent: Page/Page column 19-20
[2] Patent: WO2010/43877, 2010, A1, . Location in patent: Page/Page column 51; 52
[3] Patent: WO2007/25307, 2007, A2, . Location in patent: Page/Page column 309
[4] Patent: WO2017/35353, 2017, A1, . Location in patent: Paragraph 0759
[5] Patent: CN107954990, 2018, A, . Location in patent: Paragraph 0080; 0082; 0083; 0153; 0222
[6] Patent: WO2008/106139, 2008, A1, . Location in patent: Page/Page column 478-479

2
[ 84348-39-0 ]
[ 84348-38-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With lithium hydroxide monohydrate; water In ethanol at 25℃; for 3 h;	[002981 A mixture of (5)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate (0.5 g, 2.immol), ethanol (5 mL) and a solution of LiOH.H20 (0.44 g, 10.5 mmol) in water (5 mL) was stirred at 25 °C for 3 hours. After the reaction was fininshed, the mixture was diluted with water (40 mL), and extracted with EtOAc (50 mLx 3). The organic phases were discarded. The water phase was adjusted to pH 4-5, then extracted with EtOAc (50 mLx 3), and the combined organic phases were washed with satured brine (80 mL), dried over anhydrous Na2504, and concentrated in vacuo to give the title compound as a white solid (0.2 g, 85percent).MS (ESI, pos.ion) m/z: 128.4 [M+Hi00fb; and‘H NMR (400 MHz, CDC13): 9.08 (br, 1H), 5.00 (s, 2H), 4.58-4.46 (m, 1H),4.08-3.90 (m, 2H), 2.99-2.87 (m, 1H), 2.74-2.60 (m, 1H), 1.41 (s, 9H).

Reference： [1] Patent: WO2015/74546, 2015, A1, . Location in patent: Paragraph 00298
[2] Journal of Organic Chemistry, 1992, vol. 57, # 7, p. 2060 - 2065

3
[ 1779-49-3 ]
[ 84348-37-8 ]
[ 84348-38-9 ]

Reference： [1] Patent: US2010/272681, 2010, A1,

4
[ 144422-81-1 ]
[ 84348-38-9 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 31, p. 6529 - 6536

5
[ 144422-80-0 ]
[ 84348-38-9 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 31, p. 6529 - 6536

6
[ 144423-03-0 ]
[ 84348-38-9 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 31, p. 6529 - 6536

7
[ 24424-99-5 ]
[ 20309-87-9 ]
[ 84348-38-9 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 31, p. 6529 - 6536

8
[ 15761-39-4 ]
[ 27200-84-6 ]
[ 84348-38-9 ]

Reference： [1] Canadian Journal of Chemistry, 1982, vol. 60, # 23, p. 2903 - 2907

9
[ 84348-38-9 ]
[ 364750-81-2 ]

Reference： [1] Patent: WO2012/18325, 2012, A1, . Location in patent: Page/Page column 146

[ 84348-38-9 ] Synthesis Path-Downstream 1~88

1
[ 186581-53-3 ]
[ 84348-38-9 ]
[ 84348-39-0 ]

Reference： [1]Canadian Journal of Chemistry,1982,vol. 60,p. 2903 - 2907

2
[ 15761-39-4 ]
[ 27200-84-6 ]
[ 84348-38-9 ]

Reference： [1]Canadian Journal of Chemistry,1982,vol. 60,p. 2903 - 2907

3
[ 24424-99-5 ]
[ 20309-87-9 ]
[ 84348-38-9 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 6529 - 6536

4
[ 73984-07-3 ]
[ 84348-38-9 ]
[ 144422-82-2 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 6529 - 6536

5
[ 84348-38-9 ]
[ 20309-87-9 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 2060 - 2065

6
[ 84348-39-0 ]
[ 84348-38-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With lithium hydroxide monohydrate; water; In ethanol; at 25℃; for 3h;	[002981 A mixture of (5)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate (0.5 g, 2.immol), ethanol (5 mL) and a solution of LiOH.H20 (0.44 g, 10.5 mmol) in water (5 mL) was stirred at 25 C for 3 hours. After the reaction was fininshed, the mixture was diluted with water (40 mL), and extracted with EtOAc (50 mLx 3). The organic phases were discarded. The water phase was adjusted to pH 4-5, then extracted with EtOAc (50 mLx 3), and the combined organic phases were washed with satured brine (80 mL), dried over anhydrous Na2504, and concentrated in vacuo to give the title compound as a white solid (0.2 g, 85%).MS (ESI, pos.ion) m/z: 128.4 [M+Hi00fb; and?H NMR (400 MHz, CDC13): 9.08 (br, 1H), 5.00 (s, 2H), 4.58-4.46 (m, 1H),4.08-3.90 (m, 2H), 2.99-2.87 (m, 1H), 2.74-2.60 (m, 1H), 1.41 (s, 9H).

Reference： [1]Patent: WO2015/74546,2015,A1 .Location in patent: Paragraph 00298
[2]Journal of Organic Chemistry,1992,vol. 57,p. 2060 - 2065

7
[ 84348-38-9 ]
(5S,8S)-3-(4-Methoxy-phenyl)-1-oxa-2,7-diaza-spiro[4.4]non-2-ene-8-carboxylic acid [ No CAS ]