Hydrochloric Acid → HCID 178486045, compound

HRID 25588Notes

Reaction equation

HRID 25588 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])[CH2:7][CH2:6]1)=O.[Li+].[BH4-].Cl>C1COCC1.CCOCC>[C:16]([O:15][C:13](=[O:14])[N:11]([C@H:8]1[CH2:7][CH2:6][C@H:5]([CH2:3][OH:2])[CH2:10][CH2:9]1)[CH3:12])([CH3:17])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 178501226HCID 178501226, compound

Product 1

HCID 178486045HCID 178486045, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

17.1 g (62.95 mmol) of trans-4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexanecarboxylic acid methyl ester, dissolved in 150 ml of THF, were treated with 2.74 g (126 mmol) LiBH4. The reaction-mixture was stirred under reflux for 6 h and then 200 ml of 1N HCl were dropped to the solution under ice-cooling. The mixture was dissolved in ether and washed with water. The solvent was evaporated under reduced pressure yielding 16.2 g trans-(4-Hydroxymethyl-cyclo-hexyl)-methyl-carbamic acid tert-butyl ester.

Workup

  1. temperatureunder reflux for 6 h
  2. temperaturecooling
  3. washwashed with water
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-041ea057001443659316a72056f064eb
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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