HCID 178453922, compound → HCID 178511524, compound

HRID 1984933Notes

Reaction equation

HRID 1984933 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:10][CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[NH:16][CH2:15][CH2:14][C@H:11]1[CH2:10][CH2:9][C@@H:8]([NH2:7])[CH2:13][CH2:12]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 178453922HCID 178453922, compound

Product 1

HCID 178511524HCID 178511524, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of cis-[4-(2-benzyloxycarbonylamino-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (5.26 g, 14 mmol) in 50% TFA in CH2Cl2 (60 mL) was stirred at ambient temperature for 1 hr. The mixture was concentrated and the residue was diluted with saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (therr times). The organic layer was dried over Na2SO4 and concentrated to give cis-[2-(4-amino-cyclohexyl)-ethyl]-carbamic acid benzyl ester (3.5 g, 91%) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with CH2Cl2 (therr times)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-466a9ac5b15140f08d499d89d4397345
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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