Cerium(III) chloride → benzyl (2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidine-1-carboxylate

HRID 906966Notes

Reaction equation

HRID 906966 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH:5]1([Mg]Br)[CH2:7][CH2:6]1.C1COCC1.[CH3:15][C@H:16]1[C:20](=[O:21])[CH2:19][CH2:18][N:17]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>>[CH:5]1([C@:20]2([OH:21])[CH2:19][CH2:18][N:17]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[C@H:16]2[CH3:15])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 24636Cerium(III) chlorideHCID 59556933benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylateHCID 178420628HCID 178420628, compound

Product 1

HCID 59273039benzyl (2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidine-1-carboxylate

Procedure

By an operation in the same manner as in Reference Example 3 and using cerium chloride (11.1 g), 0.5 mol/L cyclopropylmagnesium bromide—THF solution (72.0 mL) and benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (3.0 g), the title compound was obtained as colorless oil (yield: 1.64 g, yield: 46%).

Sources & evidence

ORD record
ord-6286d3c951bb4a45a33ba6c2a8cfca17
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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