Water → (RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid methyl ester

HRID 859211Notes

Reaction equation

HRID 859211 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][CH:9]=2)[C:5](=[O:23])[CH2:4]1.C(N(CC)CC)C.Cl[C:32]([O:34][CH3:35])=[O:33].O>ClCCl>[CH3:35][O:34][C:32](=[O:33])[NH:2][CH:3]1[CH2:4][C:5](=[O:23])[N:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:12][CH:13]=2)[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 68614460(RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride

Product 1

HCID 10428462(RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid methyl esterYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 250 mg (0.74 mmol) of (RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride [Example 1f)] in 12 ml of dichloromethane is cooled to 0° C. and successively treated with 226 μl (1.6 mmol) of triethylamine and 64 μl (0.8 mmol) of methyl chloroformate. The mixture is left to warm to RT and stirred for 1 hour. For the working-up, dichloromethane and water are added to the reaction mixture. The organic layer is separated, dried over sodium sulfate, and evaporated. There are obtained 203 mg (76% of theory) of (RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid methyl ester as a white solid. MS: m/e=359 (M+H)+.

Workup

  1. waitThe mixture is left
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-68e38b5ce4c8483bb4f257f2c42c5b93
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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