Methanol → Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

HRID 75141

반응식

HRID 75141 반응식
[C:1]12([C:11]([NH2:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(C)C.CO>C1COCC1>[C:1]12([CH2:11][NH2:13])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

참가 물질

5

반응물 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 21686Tricyclo(3.3.1.13,7)decane-1-carboxamide

생성물 1

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamine수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of admantane-1-carboxamide (2 g, 11.17 mmol) in THF (50 mL) was added BH3.Me2S (10.2 M, 3.4 mL, 34.7 mmol) under nitrogen. The mixture was heated at reflux overnight. The solution was cooled to rt. Methanol (20 mL) was added to the solution. The mixture was concentrated under vacuum to give crude product, which was purified by chromatography on silica gel to afford (1-adamantyl)methylamine (1.09 g, 59%). 1H NMR (CDCl3, 400 MHz): δ=1.44-1.96 (m, 15H), 2.30 (s, 2H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under vacuum
  4. customto give crude product, which
  5. customwas purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-6ea67caa19ef43d084cf1bbdb95ce0e3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835426B2

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