Water → (3S,6R)-3-aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one

HRID 1358921ノート

反応式

HRID 1358921 の反応式
C(OC([NH:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][NH:11][C:10]1=[O:24])=O)(C)(C)C.C[Si](I)(C)C.O>C(Cl)Cl.CO>[NH2:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][Si:17]([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:18])[CH3:19])[CH2:12][NH:11][C:10]1=[O:24]

参加物

6

反応物 3

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 11728063[(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 10858173(3S,6R)-3-aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one収率 96%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one (8.0 g, 22 mmol) is dissolved in 40 mL of CH2Cl2 and cooled to −78° C. Trimethylsilyl iodide (3.5 mL, 24.5 mmol) is added slowly. The mixture is allowed to react at −78° C. for 30 min. The reaction is warmed to 0° C. and stirred for 15 min. The solution turned yellow. The reaction is quenched with NH4HCO3 (3.43 g, 44 mmol) dissolved in 30 mL of CH3OH, and 15 mL water. The mixture is concentrated and chromatographed with a 95:5 mixture of CH2Cl2 and methanol to yield 5.45 g (96%) of (3S,6R)-3-aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one as a white solid: 1H NMR (CDCl3) δ 5.61 (s, 1H), 3.88 (s, 1H), 3.42 (d, J=8 Hz, 1H), 3.32(dd, J=6 Hz and 16 Hz, 1H), 3.06 (m, 1H), 1.87 (m, 2H), 1.76 (m, 1H), 1.65 (s, 3H), 0.83 (s, 9H), 0.001 (s, 6H).

後処理

  1. customto react at −78° C. for 30 min
  2. temperatureThe reaction is warmed to 0° C.
  3. concentrationThe mixture is concentrated
  4. customchromatographed with a 95:5 mixture of CH2Cl2 and methanol

出典と根拠

ORDレコード
ord-a4a256f6a2b2401d97057b2545391dfe
出典データセット
uspto-grants-2003_07
特許番号
US06599898B2

反応ノート

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