Dimethyl Carbonate → Methyl (3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylate

HRID 1992671Notes

Reaction equation

HRID 1992671 reaction equation
C([C@H]1COC(=O)N1C([C@H:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:19][N:18]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:17]1)=O)C1C=CC=CC=1.[C:35](=O)([O:38]C)[O:36][CH3:37].C[O-].[Na+]>ClCCl>[CH2:28]([N:18]1[CH2:19][C@@H:20]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[C@H:16]([C:35]([O:36][CH3:37])=[O:38])[CH2:17]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 59131050(4S)-4-Benzyl-3-{[(3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidin-3-yl]carbonyl}-1,3-oxazolidin-2-one

Product 1

HCID 59131036Methyl (3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (4S)-4-benzyl-3-{[(3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidin-3-yl]carbonyl}-1,3-oxazolidin-2-one, from preparation 24 (2.51 g, 5.28 mmol) and dimethyl carbonate (2.22 mL, 26.4 mmol) in dichloromethane (40 mL) was added sodium methoxide (1.42 g, 26.4 mmol) at room temperature. The reaction mixture was stirred for 24 hours and diluted with dichloromethane (50 mL). The phases were separated and the organic phase was washed with water (2×40 mL), dried over magnesium sulfate and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using ethyl acetate:pentane (5:95-20:80) as eluent to afford the desired product as a colourless oil, 1.61 g (79%).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water (2×40 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-30480a198ec145d8b7221e56b4ed8815
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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