Azobisisobutyronitrile → (S)-2,2-dimethyl-4-(1-methyl-2-phenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1911523Notes

Reaction equation

HRID 1911523 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([CH3:31])(OC(OC2C=CC=CC=2)=S)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([CH3:31])=[CH:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 86623840(R)-2,2-dimethyl-4-(1-methyl-1-phenoxythiocarbonyloxy-2-phenyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 68717187(S)-2,2-dimethyl-4-(1-methyl-2-phenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl esterYield 59.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of crude (R)-2,2-dimethyl-4-(1-methyl-1-phenoxythiocarbonyloxy-2-phenyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester (700 mg) in toluene (5 ml) was treated under an argon atmosphere with 2,2′ azobis(2-methylproponitrile) (122 mg) and tri-N-butyltin hydride (0.79 ml). The reaction mixture was refluxed for 30 min, then cooled to r.t. and then directly purified by column chromatography (silica gel, gradient: cyclohexane ->cyclohexane/EtOAc 10:1) to give (S)-2,2-dimethyl-4-(1-methyl-2-phenyl-vinyl)-oxazo-lidine-3-carboxylic acid tert-butyl ester (279 mg, 59%) as light yellow waxy solid. MS (ISP): 318.3 ([M+H]+))

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. customdirectly purified by column chromatography (silica gel, gradient: cyclohexane ->cyclohexane/EtOAc 10:1)

Sources & evidence

ORD record
ord-97ec7b7a0fd04ff79acef5953677a448
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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