Ammonium Hydroxide → 2-{bicyclo[2.2.1]heptan-2-yl}acetamide

A solution of 2-(bicyclo[2.2.1]heptan-2-yl)acetic acid (0.50 g, 3.24 mmol) in DCM (30 mL) was treated with oxalyl chloride (0.426 mL, 4.86 mmol), followed by a catalytic amount of DMF (1 drop) and stirred at RT for 2 h. A solution of NH4OH (˜15M, 2 mL, ˜30 mmol) in THF (5 mL) was added drop wise and the mixture stirred at RT overnight. The mixture was concentrated to dryness and the residue was dissolved in EtOAc, washed with brine, dried over MgSO4 and concentrated to dryness to afford 2-(bicyclo[2.2.1]heptan-2-yl)acetamide (480 mg, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.19 (s, 1H), 6.65 (s, 1H), 2.14 (s, 1H), 1.91 (m, 3H), 1.75 (m, 1H), 1.35 (m, 4H), 1.11 (m, 4H); MS (ESI) m/z: 154.2 (M+H+).

1. stirringthe mixture stirred at RT overnight
2. concentrationThe mixture was concentrated to dryness
3. dissolutionthe residue was dissolved in EtOAc
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated to dryness

ORD record

ord-9bedf5c9e5d1435ead71d17ad91174b0

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2