Reaction equation
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[BH4-].[Na+].[NH4+].[Cl-].O>CO>[OH:2][CH2:1][C@@H:3]1[CH2:5][C@H:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]Participants
Procedure
To a solution of ethyl 2-formyl-1-cyclopropanecarboxylate (1.5 eq.) in methanol (0.7 M) at 0° C. was added sodium borohydride (1.5 eq.) in portions over 30 min. The mixture was allowed to stir at rt for 1.5 h and then cooled in an ice bath. Saturated aqueous NH4Cl solution was added dropwise, and the mixture was stirred for 1.5 h. Water was added, and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated to afford a racemic mixture of the title compound as a clear oil. Racemic trans 2-(hydroxymethyl)cyclopropanecarboxylate was purified by a Chiral Pak AD preparative column (10% EtOH/Hex) to afford two enantiomers. Ethyl (1R,2R)-2-(hydroxymethyl)cyclopropanecarboxylate was eluted as the faster enantiomer (retention time=12.94 min).
Workup
- temperaturecooled in an ice bath
- stirringthe mixture was stirred for 1.5 h
- extractionthe aqueous layer was extracted with EtOAc
- washThe combined organic extracts were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customto afford
Sources & evidence
- ORD record
- ord-481c4fb409f34d669adb731adb461764
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076359B2
Linked notes
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