tert-butyl (1S,2R)-1-benzyl-3-[(cyclohexyloxy)amino)-2-hydroxypropylcarbamate → (2R,3S)-3-amino-1-[(cyclohexyloxy)amino]-4-phenyl-2-butanol

HRID 29201Notes

Reaction equation

HRID 29201 reaction equation
[CH2:1]([C@H:8]([NH:20]C(=O)OC(C)(C)C)[C@H:9]([OH:19])[CH2:10][NH:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[NH2:20][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([OH:19])[CH2:10][NH:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

3

Reactant 1

HCID 54192664tert-butyl (1S,2R)-1-benzyl-3-[(cyclohexyloxy)amino)-2-hydroxypropylcarbamate

Product 1

HCID 57061218(2R,3S)-3-amino-1-[(cyclohexyloxy)amino]-4-phenyl-2-butanolYield 97%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A combination of trifluoroacetic acid (20 mL) and tert-butyl (1S,2R)-1-benzyl-3-[(cyclohexyloxy)amino]-2-hydroxypropylcarbamate (2.00 g, 5.29 mmol) was stirred under Argon at ambient temperature for approximately 30 minutes. The reaction was evaporated in vacuo and the residue was partitioned between dichloromethane and aqueous sodium hydroxide (1N). After separating the layers, the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a solid which was dried under high vacuum to provide (2R,3S)-3-amino-1-[(cyclohexyloxy)amino]-4-phenyl-2-butanol (1.426 g, 97%). H1-NMR (chloroform-D3): 1.24 (m, 5H), 1.58 (m, 4H), 1.73 (m, 2H), 1.95 (m, 2H), 2.51 (m, 1H), 2.97 (m, 2H), 3.16 (m, 2H), 3.33 (m, 1H), 3.57 (m, 1H), 3.77 (m, 1H), 7.26 (m, 5H). MS(ESI): 279(M+H).

Workup

  1. customThe reaction was evaporated in vacuo
  2. customthe residue was partitioned between dichloromethane and aqueous sodium hydroxide (1N)
  3. customAfter separating the layers
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a solid which
  8. customwas dried under high vacuum

Sources & evidence

ORD record
ord-062f71e8b9004ce0922015d99de9eb8b
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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