(2S,3S)-2-t-butoxycarbonylamino-1-cyclohexyl-3-hydroxy-5-methylhexane → (2S,3S)-2-amino-1-cyclohexyl-3-hydroxy-5-methylhexane

HRID 2396145Notes

Reaction equation

HRID 2396145 reaction equation
C(OC([NH:8][C@H:9]([C@@H:17]([OH:22])[CH2:18][CH:19]([CH3:21])[CH3:20])[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:22])[CH2:18][CH:19]([CH3:20])[CH3:21])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

3

Reactant 1

HCID 57261833(2S,3S)-2-t-butoxycarbonylamino-1-cyclohexyl-3-hydroxy-5-methylhexane

Product 1

HCID 22861533(2S,3S)-2-amino-1-cyclohexyl-3-hydroxy-5-methylhexaneYield 100.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S,3S)-2-t-butoxycarbonylamino-1-cyclohexyl-3-hydroxy-5-methylhexane (120 mg) in trifluoroacetic acid (3 ml) was stirred at 0° C. for 30 minutes. After evaporation of the solvent, the residue was dissolved in ethyl acetate (10 ml). The solution was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfate, and evaporated in vacuo to give (2S,3S)-2-amino-1-cyclohexyl-3-hydroxy-5-methylhexane (82 mg) as an oil. Rf: 0.30 (chloroform: methanol: acetic acid, 16:1:1, V/V)

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  3. washThe solution was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-510f04a479724d008b74098e86518c92
Source dataset
uspto-grants-1996_02
Patent number
US05491132

Reaction notes

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