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

HRID 130616

반응식

HRID 130616 반응식
[BH4-].[Na+].Cl[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 23158970Ditert-butyl 1-chlorocyclopropane-1,2-dicarboxylate

생성물 1

HCID 23158971Di-tert-butyl cyclopropane-1,2-dicarboxylate수율 96%

시약·촉매·용매 2

HCID 517166Dichlorocobalt hexahydrate촉매HCID 31374Dimethylacetamide용매2회

실험 절차

Sodium borohydride (103 mg, 1.81 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-chlorocyclopropane-1,2-dicarboxylate (cis/trans=26/74) (hereinafter the compound will be referred to as “compound (4b)”) (500 mg, 1.81 mmol) at 10° C. Cobalt chloride hexahydrate (2.4 mg, 0.010 mmol) was added to the resultant solution at the same temperature. After completion of addition, the resultant mixture was stirred at 40° C. for six hours. After completion of reaction, the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL, to thereby yield a solution containing 418.8 mg (yield: 96%) 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. customthe whole reaction mixture
  5. additionwas diluted with an HPLC mobile phase to 50 mL
  6. customto thereby yield a solution

출처 및 근거

ORD 기록
ord-a200717bb849434e8ad323295c482c61
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381833B2

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