Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → HCID 59437175, 화합물

HRID 75157

반응식

HRID 75157 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 59437175HCID 59437175, 화합물수율 42.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b12f6b0d30474bdbb69a09795a73ce18
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835426B2

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