Cerium(III) chloride → tert-butyl (2S,3R)-3-hydroxy-2-methyl-3-vinylpyrrolidine-1-carboxylate

HRID 906967Notes

Reaction equation

HRID 906967 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH:5]([Mg]Br)=[CH2:6].C1COCC1.[CH3:14][C@H:15]1[C:19](=[O:20])[CH2:18][CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>>[OH:20][C@@:19]1([CH:5]=[CH2:6])[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:15]1[CH3:14]

Participants

4

Reactant 3

HCID 24636Cerium(III) chlorideHCID 59273045tert-butyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylateHCID 178420667HCID 178420667, compound

Product 1

HCID 59273002tert-butyl (2S,3R)-3-hydroxy-2-methyl-3-vinylpyrrolidine-1-carboxylate

Procedure

By an operation in the same manner as in Reference Example 3 and using cerium chloride (3.95 g), 1 mol/L vinylmagnesium bromide—THF solution (12.5 mL) and tert-butyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (1.0 g), the title compound was obtained as colorless oil (yield: 0.648 g, yield: 57%).

Sources & evidence

ORD record
ord-5535c92f906c4518b175072ebc2ecd59
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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