1-Aminocyclohexanecarboxylic acid → (1-Aminocyclohexyl)methanol

HRID 398817

Reaction equation

HRID 398817 reaction equation
[NH2:1][C:2]1([C:8](O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.B(F)(F)F.CCOCC.B#B.[OH-].[Na+]>C1COCC1.O.C1COCC1>[NH2:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 6328200Diboron

Product 1

HCID 409153(1-Aminocyclohexyl)methanolYield 73.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c0bd5afdf5d24bb9be41dc17dd574719
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Linked notes

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