2(S)-t-butoxycarbonylamino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane → 2(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane

HRID 1588832Notes

Reaction equation

HRID 1588832 reaction equation
C(OC([NH:8][C@H:9]([C@@H:17]([OH:23])[CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C@H:9]([C@@H:17]([OH:23])[CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

3

Reactant 1

HCID 156312702(S)-t-butoxycarbonylamino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane

Product 1

HCID 146717222(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptaneYield 98.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2(S)-t-butoxycarbonylamino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (600 mg) in trifluoroacetic acid (10 ml) was stirred at 0° C. for 30 minutes. After evaporation of the solvent, the residue was dissolved in ethyl acetate (20 ml). The solution was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, and evaporated in vacuo to give 2(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (412 mg) as an oil.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washThe solution was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7bf1a8e02c7e47248cf291006d70599e
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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