Triethylsilane → HCID 86584836, compound

HRID 458316Notes

Reaction equation

[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13]CC2C=CC(OC)=CC=2)[CH2:10][C@H:9]1[CH2:23][CH2:24][CH2:25][N:26]1[CH:30]=[CH:29][CH:28]=[CH:27]1)=[O:7])[CH2:2][CH2:3][CH3:4].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([SH:13])[CH2:10][C@@H:9]1[CH2:23][CH2:24][CH2:25][N:26]1[CH:27]=[CH:28][CH:29]=[CH:30]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

(Method 1): A solution of 0.065 g (0.151 mmol) (2R,4R)-4-(4-methoxy-benzylsulfanyl)-2-(3-pyrrol-1-yl-propyl)-pyrrolidine-1-carboxylic acid butyl ester was dissolved in 2 ml TFA, cooled to 0° C. and treated with 0.24 ml (1.51 mmol) triethylsilane, stirred for 22 h at room temperature and treated again with 0.24 ml (1.51 mmol) triethylsilane after further 30 h the evaporated residue was purified by flash silica gel column (CH2Cl2/EtOAc 99:1) to give 10 mg of (2S,4R)-4-mercapto-2-(3-pyrrol-1-yl-propyl)-pyrrolidine-1-carboxylic acid butyl ester, MS: 311 (MH+).

Workup

customwas purified by flash silica gel column (CH2Cl2/EtOAc 99:1)

Sources & evidence

ORD record: ord-860fa153d47e49e588fcb92cfba3e8c5
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189756B2

Reaction notes

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