Triethylamine → (2S,4R)-N-allyloxycarbonyl-4-methanesulfonyloxyproline methyl ester

HRID 1090504Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[C:13]([O:15][CH3:16])=[O:14])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:9][C@H:8]1[C:13]([O:15][CH3:16])=[O:14])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine (210.2 g) and triethylamine (150.2 ml) in dichloromethane (2 l) was added dropwise methanesulfonyl chloride (70.7 ml) at 0° C. After stirring for 1 hour at 0° C., the reaction mixture was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-methanesulfonyloxypyrrolidine (281.8 g).

Workup

washthe reaction mixture was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-dee208467d614706abef595ec7bb9d38
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081237

Reaction notes

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