(r)-2-[(4s,5s)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hex-(z)-ylidene-pyrrolidine-1-carboxylic acid tert-butyl ester → (r)-2-[(4s,5s)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hexyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732592Notes

Reaction equation

HRID 732592 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12]/[C:11](=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])/[CH2:10][C@@H:9]1[C@H:19]1[O:23][C:22]([CH3:25])([CH3:24])[N:21]([C:26](=[O:28])[CH3:27])[C@H:20]1[CH2:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][C@@H:9]1[C@H:19]1[O:23][C:22]([CH3:25])([CH3:24])[N:21]([C:26](=[O:28])[CH3:27])[C@H:20]1[CH2:29][C:30]1[CH:31]=[C:32]([F:37])[CH:33]=[C:34]([F:36])[CH:35]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 68818416(r)-2-[(4s,5s)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hex-(z)-ylidene-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 68815992(r)-2-[(4s,5s)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hexyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Combine (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hex-(Z)-ylidene-pyrrolidine-1-carboxylic acid tert-butyl ester (0.04 g, 0.076 mmol), 10% palladium on carbon (4 mg) and methanol (2 mL) and stir for 2 days under 1 atmosphere of hydrogen. Add filter agent, filter and concentrate under reduced pressure to provide the desired compound as a mixture of isomers (2:1 4(S):4(R); 0.036 g, 90%). Subject isomer mixture to HPLC chromatography under acidic conditions: TFA 0.05% at pH 2.5; Organic solvent: acetonitrile; Gradient from 90 to 95% acetonitrile.

Workup

  1. additionAdd
  2. filtrationfilter agent
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-596b0beeb0204f4589feaf5fe1eee294
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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