Methyl iodide → HCID 56998705, compound

HRID 975660Notes

Reaction equation

HRID 975660 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24])=[O:6])[CH:2]=[CH2:3].[CH:25](N(C(C)C)CC)(C)C.CI>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH3:25])[CH2:20][C:19]1=[O:24])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 54136579HCID 54136579, compound

Product 1

HCID 56998705HCID 56998705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-(2-oxo-piperazin-1-yl) methyl-4-(methanesulfonyloxy)pyrrolidine (6.37 g) in dichloromethane (60 ml) were added N,N-diisopropyl-N-ethylamine (3.38 ml) and methyl iodide (1.64 ml) under ice cooling with stirring, and the mixture was allowed to stay in a refrigeration for 12 hours. The mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of ethyl acetate, methanol and isopropylamine (10:1:0.3 v/v/v) to give (2S,4R)-1-allyloxycarbonyl-2-(2-oxo-4-methylpiperazin-1-yl) methyl-4-(methanesulfonyloxy)pyrrolidine (3.19 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with a mixture of ethyl acetate, methanol and isopropylamine (10:1:0.3 v/v/v)

Sources & evidence

ORD record
ord-5eb429dc9e554e3c903c2b2b8c5d1456
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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