Triethylsilane → HCID 86590060, compound

HRID 1006834Notes

Reaction equation

HRID 1006834 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][C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=O)=[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][C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69432017HCID 69432017, compound

Product 1

HCID 86590060HCID 86590060, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 72 mg (0.152 mmol) (2R,4R)-2-[3-(4-fluoro-phenyl)-3-oxo-propyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester and 0.12 (1.4 mmol) triethylsilane in 2.7 ml TFA was heated for 18 h at 80° C. Evaporation followed by flash chromatography on silica gel (EtOAc/hexane 7:3) gave 8 mg (15%) (2R,4R)-2-[3-(4-fluoro-phenyl)-propyl]-4-mercapto-pyrrolidine-1-carboxylic acid butyl ester, MS: 340 (MH+).

Workup

  1. customEvaporation

Sources & evidence

ORD record
ord-fa8375b2b9624beba45ab84023381879
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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