Water → (1S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enylamine

HRID 402534노트

반응식

HRID 402534 반응식
[N:1]([C@H:4]1[CH2:8][C@@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:6]=[CH:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[Cl-].[Na+]>O1CCCC1>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][C@@H:7]1[CH2:8][C@H:4]([NH2:1])[CH:5]=[CH:6]1)([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 86639599((1R,4S)-4-Azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane

생성물 1

HCID 59224828(1S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enylamine수율 106.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

934 mg (3.90 mmol) of ((1R,4S)-4-azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane (35) were dissolved in 16 mL of tetrahydrofuran and 1.13 g (4.29 mmol) of triphenylphosphine were added. After the addition of 2 mL of water, the reaction mixture was stirred at room temperature, until the reaction was complete. Sat. sodium chloride solution was added, the layers separated and the organic layer was evaporated in vacuo. The crude product was purified by silica gel chromatography to yield 890 mg of the title compound (36). Rt=1.02 min (Method C). Detected mass: 214.3 (M+H+).

후처리

  1. customthe layers separated
  2. customthe organic layer was evaporated in vacuo
  3. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-22d08b3ff24741c9ba8ea844fc34e97e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742116B2

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