Water → trans-(2-Aminocyclohexyl)methanol

HRID 1848044Notes

Reaction equation

HRID 1848044 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14](O)=[O:15].O.[OH-].[Na+]>C1COCC1>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2724640trans-2-Aminocyclohexanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2724655trans-(2-Aminocyclohexyl)methanolYield 19.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of LiAlH4 (796 mg, 20.97 mmol) in anhydrous THF (20 mL) at rt was added portion-wise (1R,2R)-2-aminocyclohexanecarboxylic acid (1 g, 6.99 mmol). The mixture was heated at 80° C. for 4 h before it was cooled to 0° C. Water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. The mixture was filtered and the filtrate partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate. The organic layer was separated and washed with 1M aq NaOH. The organic layer was separated, dried over MgSO4, filtered, and under reduced pressure to afford ((1R,2R)-2-aminocyclohexyl)methanol (180 mg) which was not purified further. LCMS (ESI) m/z 130 (M+H)+.

Workup

  1. temperaturewas cooled to 0° C
  2. filtrationThe mixture was filtered
  3. customthe filtrate partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate
  4. customThe organic layer was separated
  5. washwashed with 1M aq NaOH
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-fa9c79dbe6d44b3784393d85d9192e05
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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