1-Aminocyclohexanecarboxylic acid → (1-Aminocyclohexyl)methanol

Temperature

40 °C

1-Amino-1-cyclohexanecarboxylic acid(51.5 g, Aldrich) was added to 150 ml of THF followed by boron trifluoride etherate(27 ml, Aldrich). The reaction mixture was heated to 40° C., stirred for 10 minutes and then a 1.0M solution of diborane(380 ml, Aldrich) was added. The mixture was refluxed for 2 hr, cooled and added THF/water (1:1,25 ml) followed by 6N NaOH(95 ml). The reaction mixture was refluxed for 2 hr, cooled to room temperature and the organic layer was separated, washed with brine, dried and concentrated to give a light yellow oil (34.0 g). 1H NMR consistent with the proposed structure.

1. temperatureThe mixture was refluxed for 2 hr
2. temperaturecooled
3. temperatureThe reaction mixture was refluxed for 2 hr
4. temperaturecooled to room temperature
5. customthe organic layer was separated
6. washwashed with brine
7. customdried
8. concentrationconcentrated

ORD record

ord-c0bd5afdf5d24bb9be41dc17dd574719

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05817652