N-(5-(hydroxymethyl)bicyclo[3.2.1]octan-1-yl)acetamide → (5-Aminobicyclo[3.2.1]octan-1-yl)methanol

HRID 1503249Notes

Reaction equation

HRID 1503249 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][C:7]([NH:11]C(=O)C)([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2>C(O)C.[Pd]>[NH2:11][C:7]12[CH2:10][C:3]([CH2:2][OH:1])([CH2:9][CH2:8]1)[CH2:4][CH2:5][CH2:6]2

Participants

4

Reactant 1

HCID 117702687N-(5-(hydroxymethyl)bicyclo[3.2.1]octan-1-yl)acetamide

Product 1

HCID 84072201(5-Aminobicyclo[3.2.1]octan-1-yl)methanolYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(5-(hydroxymethyl)bicyclo[3.2.1]octan-1-yl)acetamide (3.70 g, 12.8 mmol) in ethanol (30 mL) was added Pd/C (371 mg) and the reaction mixture was hydrogenated at room temperature (1 atm) overnight. The catalyst was then removed by filtration and the filtrate was concentrated under reduced pressure to afford 1.88 g (95%) of the title compound, (5-aminobicyclo[3.2.1]octan-1-yl)methanol as a brown oil. ESI-MS m/z: 156 (M+H)+.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(1 atm) overnight
  3. customThe catalyst was then removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-09b0f9d18b7447c7be9fc02d44bd4ecb
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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