Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate → tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

HRID 539969노트

반응식

HRID 539969 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12](OC)=[O:13])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[OH:13][CH2:12][C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11]1

참가 물질

4

반응물 2

HCID 546046Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylateHCID 4148881Lithium borohydride

생성물 1

HCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate수율 76.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a cooled solution of methyl 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylate (1.2 g, 5.6 mmol) in tetrahydrofuran (10 mL) at 0° C. was added dropwise a solution of lithium borohydride (244 mg, 11.2 mmol) in tetrahydrofuran (10 mL) The reaction mixture was allowed to warm to room temperature and stirred at this temperature overnight. The reaction was quenched by addition of water (10 mL) and the resulting mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 0.8 g of the product (yield was 76.2%).

후처리

  1. customThe reaction was quenched by addition of water (10 mL)
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3965613a7bc948b996b16850d8fb5a03
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

반응 노트

불러오는 중…