Water → HCID 178484806, compound

HRID 25565Notes

Reaction equation

HRID 25565 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](OC(C)(C)C)=O)[CH2:13][CH2:12]1)=O.O>C1COCC1>[CH3:18][NH:17][C@H:14]1[CH2:15][CH2:16][C@H:11]([CH2:9][OH:8])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178501239HCID 178501239, compound

Product 1

HCID 178484806HCID 178484806, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 1.52 g (40 mmol) LAH in 7 ml THF was refluxed and treated for 2.5 h with a solution of 5.15 g (20 mmol) of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid methyl ester in 35 ml THF. The reaction was heated for 15 h, cooled (0° C.) and hydrolyzed with 10 ml water. The mixture was diluted with THF, dried over Na2SO4, filtered and evaporated. The residue was dissolved in CH2Cl2, dried over Na2SO4, filtered and evaporated to yield 2.89 g (100%) of trans-(4-Methylamino-cyclohexyl)-methanol, mp: 87-88° C.; MS: 143 (M).

Workup

  1. temperatureThe reaction was heated for 15 h
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-01a373d24b254466a59beb1624054893
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

Loading…