Ethanol → (1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine

HRID 2092863Notes

Reaction equation

HRID 2092863 reaction equation
[OH-].[Na+].FC(F)(F)C([NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O.CCO>>[NH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 87320949cis-tert-Butyl 2-(2,2,2-trifluoroacetamido)cyclohexylcarbamate

Product 1

HCID 1514392(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine

Procedure

Aqueous sodium hydroxide (50%, 10 g, 0.125 mole, 5.7 eq) was added to a solution of cis-tert-butyl 2-(2,2,2-trifluoroacetamido)cyclohexylcarbamate in EtOH (about 21.9 mmol). An exotherm from 20 to 37° C. was observed and a fine white slurry formed. The reaction mixture was stirred overnight, during which further solids precipitated out of solution. The solvent volume was concentrated under reduced pressure to about 10 to 15 mL and then IPAc (40 mL) and water (30 mL) were added to form a clean bi-phasic solution. Following phase separation the aqueous phase was extracted with IPAc (15 mL) and the organic extracts were combined and washed with water (15 mL) to give the title compound as a crude racemic product in IPAc.

Workup

  1. customfrom 20 to 37° C.
  2. customa fine white slurry formed
  3. customprecipitated out of solution
  4. concentrationThe solvent volume was concentrated under reduced pressure to about 10 to 15 mL
  5. additionIPAc (40 mL) and water (30 mL) were added
  6. customto form a clean bi-phasic solution
  7. customFollowing phase separation the aqueous phase
  8. extractionwas extracted with IPAc (15 mL)
  9. washwashed with water (15 mL)

Sources & evidence

ORD record
ord-5914df57638e403c997a9ec07e44e44f
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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