Triphenylphosphine → tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39]([N:41]1[CH2:45][CH2:44][CH:43](O)[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].[C:47]([OH:50])(=[S:49])[CH3:48]>C1COCC1>[C:34]([O:38][C:39]([N:41]1[CH2:45][CH2:44][CH:43]([S:49][C:47](=[O:50])[CH3:48])[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of triphenylphosphine (2.1 g, 8 mmol) in THF (14 ml) was added dropwise (15 minutes) diisopropylazodicarboxylate (1.55 ml, 8 mmol). After 30 minutes stirring at 0° C., a solution containing (RS)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (1 g, 5.34 mmol) and thioacetic acid (0.57 ml, 8 mmol) in THF (7 ml) was added dropwise. The reaction mixture was stirred 30 minutes at 0° C., 45 minutes at room temperature and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1 then 8:2 then 1:1) to provide (RS)-3-acetylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.4 g, 100%) as a slightly yellow oil, MS: m/e=246.3 (M+H+).
Workup
- additionwas added dropwise
- stirringThe reaction mixture was stirred 30 minutes at 0° C., 45 minutes at room temperature
- concentrationconcentrated
- customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1
Sources & evidence
- ORD record
- ord-a2aed4d942d84baf945248ee5e5d30f7
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451819B2
Reaction notes
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