Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → HCID 59437175、化合物

HRID 75157

反応式

HRID 75157 の反応式
[C:1]12([CH2:11][NH2:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Si:13]([O:20][CH2:21][CH:22]1[CH2:24][N:23]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl>[Si:13]([O:20][CH2:21][C@@H:22]([NH:23][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:24][NH:12][CH2:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

参加物

4

反応物 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

生成物 1

HCID 59437175HCID 59437175、化合物収率 42.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1-adamantylmethyl)amine (15 g, 52 mmol) in anhydrous CH2Cl2 (50 mL) was added tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)aziridine-1-carboxylate (13 g, 78.3 mmol). The mixture was stirred for 10 min, the solvent was removed in vacuo and the residue was stirred at 40° C. for 5 h. The mixture was diluted with EtOAc (500 mL) and washed with water (100 mL),1N aq HCl (50 mL), satd aq NaHCO3 (50 ml) and brine (50 mL), and dried over MgSO4. The solution was concentrated to give a residue, which was purified by chromatography on silica gel to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-((1-adamantylmethyl)amino)propan-2-ylcarbamate (10 g, 24%). 1H NMR: (CDCl3, 400 MHz): δ=0.041 (s, 6H), 0.882 (s, 9H), 1.44 (s, 9H), 1.49 (s, 6H), 1.65 (m, 6H), 1.94 (s, 3H), 2.23 (s, 2H), 2.62-2.81 (m, 2H), 3.67 (m, 3H), 5.30 (s, 1H).

後処理

  1. customthe solvent was removed in vacuo
  2. stirringthe residue was stirred at 40° C. for 5 h
  3. additionThe mixture was diluted with EtOAc (500 mL)
  4. washwashed with water (100 mL),1N aq HCl (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationThe solution was concentrated
  7. customto give a residue, which
  8. customwas purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-b12f6b0d30474bdbb69a09795a73ce18
出典データセット
uspto-grants-2014_09
特許番号
US08835426B2

関連ノート

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