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

HRID 402534ノート

反応式

HRID 402534 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-22d08b3ff24741c9ba8ea844fc34e97e
出典データセット
uspto-grants-2014_06
特許番号
US08742116B2

反応ノート

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