(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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CAS No:
84348-38-9
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Formula:
C11H17NO4
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Chemical Name:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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Synonyms:
1,2-Pyrrolidinedicarboxylicacid, 4-Methylene-, 1-(1,1-diMethylethyl) ester, (2S)-;(S)-1-(tert-butoxycarbonyl)-4-Methylenepyrrolidine-2-carboxylic acid;N-tert-Butoxycarbonyl-4-methylene-L-proline;N-Boc-4-methylene-L-proline 97%;N-T-BOC-4-METHYLENE-L-PROLINE;(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;BOC-4-METHYLENE-L-PROLINE;N-Boc-4-methylene-L-proline
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CAS No:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Basic Attributes
227.26
227.115753
DTXSID70617427
2933990090
Characteristics
66.8
1
1.2±0.1 g/cm3
110-114°C
349.8°C at 760 mmHg
165.4±27.9 °C
1.513
Insoluble in water.
Safety Information
NONH for all modes of transport
3
36/37/38
26
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Use and Manufacturing
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 NaHC0To 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.NaHCO[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).
Computed Properties
Molecular Weight:227.26
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:227.11575802
Monoisotopic Mass:227.11575802
Topological Polar Surface Area:66.8
Heavy Atom Count:16
Complexity:329
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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