Reaction equation
[BH4-].[Na+].Br[C:4]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:5]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>CN(C)C(=O)C.O.O.O.O.O.O.[Co](Cl)Cl>[CH:5]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH:4]1[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]Participants
Procedure
Sodium borohydride (35.7 mg, 0.944 mmol) was added to and dissolved in N,N-dimethylacetamide (1.5 mL) at room temperature, followed by addition of an N,N-dimethylacetamide solution (1.0 mL) of di-tert-butyl 1-bromocyclopropane-1,2-dicarboxylate (cis/trans=11/89) (hereinafter the compound will be referred to as “compound (4c)”) (202 mg, 0.629 mmol) at 10° C. Without manipulating the temperature of the reaction, cobalt chloride hexahydrate (0.7 mg, 0.003 mmol) was added to the resultant solution. After completion of addition, the resultant mixture was stirred at 10° C. for 15 minutes. After completion of reaction, the entirety of the reaction mixture was diluted with an HPLC mobile phase to 20 mL, to thereby yield a solution containing 152.4 mg (yield: 100%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter).
Workup
- customat 10° C
- additionAfter completion of addition
- customAfter completion of reaction
- additionthe entirety of the reaction mixture was diluted with an HPLC mobile phase to 20 mL
- customto thereby yield a solution
Sources & evidence
- ORD record
- ord-9a7d51a64f7049b88b756a6634157761
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381833B2
Linked notes
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