[3-(Benzyloxycarbonylamino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester → (3-Amino-cyclohexylmethyl)-carbamic acid benzyl ester

HRID 352212Notes

Reaction equation

HRID 352212 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O>[CH2:19]([O:18][C:16](=[O:17])[NH:15][CH2:14][CH:10]1[CH2:11][CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 22713895[3-(Benzyloxycarbonylamino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 22714145(3-Amino-cyclohexylmethyl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [3-(benzyloxycarbonylamino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (6 g, 16.6 mmol) in TFA (30 mL) was stirred for 1.5 h. The solution was concentrated using benzene to azeotrope, diluted with EtOAc, washed (1.0 N NaOH), dried (Na2SO4), filtered, and concentrated to afford (4.2 g, 97%) as a crude solid. Mass Spectrum (ES+) (m/z) 263.1 [M+1].

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed (1.0 N NaOH)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford (4.2 g, 97%) as a crude solid

Sources & evidence

ORD record
ord-11453e1e53c1482a863b7693b5d7aae2
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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