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

HRID 1649919Notes

Reaction equation

HRID 1649919 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-5f7b986a6345468a99481fd56a1cdb88
Source dataset
uspto-grants-1990_05
Patent number
US04921855

Reaction notes

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