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

HRID 906972Notes

Reaction equation

HRID 906972 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH:5]1([Mg]Br)[CH2:7][CH2:6]1.C1COCC1.[CH2:15]([C@H:17]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH3:16]>>[CH:5]1([C@:21]2([OH:22])[CH2:20][CH2:19][N:18]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])[C@H:17]2[CH2:15][CH3:16])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 24636Cerium(III) chlorideHCID 59273038benzyl (2S)-2-ethyl-3-oxopyrrolidine-1-carboxylateHCID 178420628HCID 178420628, compound

Product 1

HCID 59273035benzyl (2S,3R)-3-cyclopropyl-2-ethyl-3-hydroxypyrrolidine-1-carboxylate

Procedure

By an operation in the same manner as in Reference Example 3 and using cerium chloride (8.64 g), 0.5 mol/L cyclopropylmagnesium bromide—THF solution (58.0 mL) and benzyl (2S)-2-ethyl-3-oxopyrrolidine-1-carboxylate (2.37 g), the title compound was obtained as colorless oil (yield: 2.01 g, yield: 73%).

Sources & evidence

ORD record
ord-5f9efdd5d01a4108a084baef6ba67fd6
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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