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

HRID 75141

Reaction equation

HRID 75141 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6ea67caa19ef43d084cf1bbdb95ce0e3
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Linked notes

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