4-Aminocyclohexanecarboxylic acid → ((1s,4s)-4-Aminocyclohexyl)methanol

HRID 2369387Notes

Reaction equation

HRID 2369387 reaction equation
[CH2:1]1[CH:6]([C:7](O)=[O:8])[CH2:5][CH2:4][CH:3]([NH2:10])[CH2:2]1.B.C1COCC1>C1COCC1>[CH2:1]1[CH:6]([CH2:7][OH:8])[CH2:5][CH2:4][CH:3]([NH2:10])[CH2:2]1

Participants

4

Reactant 2

HCID 1715604-Aminocyclohexanecarboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 424390((1s,4s)-4-Aminocyclohexyl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1r,4r)-4-aminocyclohexanecarboxylic acid (860 mg, 6.0 mmol, 1.0 eq) in THF (10 mL) was added dropwise BH3/THF (1.0 mol/L in THF, 30 mL, 5.0 equiv.) at 0° C. The reaction was allowed to warm to room temperature. The reaction was heated at reflux for 48 hours. The reaction was quenched with AcOH and concentrated in vacuo to get crude ((1r,4r)-4-aminocyclohexyl)methanol (600 mg, 78%) which was used to the next step without further purification. MS: m/z 130.1 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 hours
  3. customThe reaction was quenched with AcOH
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66303fdfd0c64d9dbc2572d8e69ecb95
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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