Cerium(III) chloride → benzyl (2S,3S)-3-hydroxy-2-methyl-3-propylpyrrolidine-1-carboxylate

HRID 906951Notes

Reaction equation

HRID 906951 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH3:5][C@H:6]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[CH2:22]([Mg]Br)[CH2:23][CH3:24].C1COCC1>>[OH:11][C@@:10]1([CH2:22][CH2:23][CH3:24])[CH2:9][CH2:8][N:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:6]1[CH3:5]

Participants

4

Reactant 3

HCID 24636Cerium(III) chlorideHCID 59556933benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylateHCID 178420656HCID 178420656, compound

Product 1

HCID 59273057benzyl (2S,3S)-3-hydroxy-2-methyl-3-propylpyrrolidine-1-carboxylate

Procedure

By an operation in the same manner as in Reference Example 3 and using cerium chloride (12.9 g), 2 mol/L propylmagnesium bromide—THF solution (20 mL) and benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (3.5 g), the title compound was obtained as pale-yellow oil (yield: 2.32 g, yield: 56%).

Sources & evidence

ORD record
ord-ac706bc776ae40cc827a813cdf876cfb
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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