Sodium borohydride → Di-tert-butyl cyclopropane-1,2-dicarboxylate

HRID 130617

반응식

HRID 130617 반응식
[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]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 23158974Di-tert-butyl 1-bromocyclopropane-1,2-dicarboxylate

생성물 1

HCID 23158971Di-tert-butyl cyclopropane-1,2-dicarboxylate수율 100%

시약·촉매·용매 2

HCID 517166Dichlorocobalt hexahydrate촉매HCID 31374Dimethylacetamide용매2회

실험 절차

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).

후처리

  1. customat 10° C
  2. additionAfter completion of addition
  3. customAfter completion of reaction
  4. additionthe entirety of the reaction mixture was diluted with an HPLC mobile phase to 20 mL
  5. customto thereby yield a solution

출처 및 근거

ORD 기록
ord-9a7d51a64f7049b88b756a6634157761
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381833B2

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