Hydrochloric Acid → HCID 178479229, compound

HRID 1984869Notes

Reaction equation

HRID 1984869 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18]C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(Cl)(Cl)[Cl:29]>CCOC(C)=O>[ClH:29].[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH2:18])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6212ChloroformHCID 178453647HCID 178453647, compound

Product 1

HCID 178479229HCID 178479229, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a suspension of trans-[4-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-carbamic acid benzyl ester (4.00 g, 11.0 mmol) in EtOAc (40 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). To the reaction mixture was added CHCl3 (10 mL) and the mixture was stirred at ambient temperature for 3 hr. To the reaction mixture was 4 M hydrogen chloride in EtOAc (20 mL) and the mixture was stirred at ambient temperature for 1.5 hr, filtered, washed with EtOAc, and dried under reduced pressure to give trans-(4-aminomethyl-cyclohexyl)-carbamic acid benzyl ester hydrochloride (2.96 g, 90%) as a white solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1.5 hr
  2. filtrationfiltered
  3. washwashed with EtOAc
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ee0641f7da684cfa916040eee16f98d3
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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