Triethylsilane → (E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]-N-methylacrylamide

HRID 2371825Notes

Reaction equation

HRID 2371825 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:9][C@H:8]1/[CH:32]=[CH:33]/[C:34]([NH:36][CH3:37])=[O:35])=[O:6])[CH:2]=[CH2:3].C([SiH](CC)CC)C>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([SH:12])[CH2:9][C@H:8]1/[CH:32]=[CH:33]/[C:34]([NH:36][CH3:37])=[O:35])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 12052TriethylsilaneHCID 67792453(E)-3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]-N-methylacrylamide

Product 1

HCID 86745544(E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]-N-methylacrylamideYield 76.3%

Procedure

The same operation as in Reference Example 4-2) was carried out by using (E)-3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]-N-methylacrylamide (the compound obtained in Reference Example 5-1); 1.54 g, 3 mmol) and triethylsilane (0.49 ml, 3.15 mmol), followed by flash column chromatographic purification on silica gel (Wakogel® C-300, 40 ml, elution with acetone-methylene chloride 1:1) to give the title compound (620 mg, 76.3% yield).

Workup

  1. customobtained in Reference Example 5-1)

Sources & evidence

ORD record
ord-81324f732af74a2894ace0b62eaba4be
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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