Triethylsilane → (2S,4S)-N-Allyloxycarbonyl-2-[(E)-2-[4-(allyloxycarbonyl)piperazinvlcarbonyl]vinyl]-4-mercaptopyrrolidine

HRID 2371830Notes

Reaction equation

HRID 2371830 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]([N:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][CH2:45][CH:46]=[CH2:47])=[O:43])[CH2:38][CH2:37]1)=[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]([N:36]1[CH2:37][CH2:38][N:39]([C:42]([O:44][CH2:45][CH:46]=[CH2:47])=[O:43])[CH2:40][CH2:41]1)=[O:35])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 12052TriethylsilaneHCID 67917267(2S,4S)-N-allyloxycarbonyl-2-[(E)-2-[4-(allyloxycarbonyl)piperazinylcarbonyl]vinyl]-4-tritylthiopyrrolidine

Product 1

HCID 86745546(2S,4S)-N-Allyloxycarbonyl-2-[(E)-2-[4-(allyloxycarbonyl)piperazinvlcarbonyl]vinyl]-4-mercaptopyrrolidineYield 100%

Procedure

The same operation as in Reference Example 4-2) was carried out by using (2S,4S)-N-allyloxycarbonyl-2-[(E)-2-[4-(allyloxycarbonyl)piperazinylcarbonyl]vinyl]-4-tritylthiopyrrolidine (the compound obtained in Reference Example 8-1); 1.97 g, 3.02 mmol) and triethylsilane (0.51 ml, 3.17 mmol), followed by flash column chromatographic purification on silica gel (Wakogel® C-300, 40 ml, elution with acetone-ethyl acetate 1:2) to give the title compound (1.24 g, 100% yield) as an oil.

Workup

  1. customobtained in Reference Example 8-1)

Sources & evidence

ORD record
ord-44904e23ea84451c8f1dd28e9f6717dd
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

Loading…