Triethylamine → N-[cis-4-(Boc-amino)cyclohexyl]methanesulfonamide

HRID 1371649Notes

Reaction equation

HRID 1371649 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

Product 1

HCID 18348373N-[cis-4-(Boc-amino)cyclohexyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (Altech, 1.24 g, 5.79 mmol) in methylene chloride (50 mL) at 0° C., triethylamine (202 mg, 6.95 mmol) and methansulfonylchloride (Aldrich, 796 mg, 6.95 mmol) were added successively and the mixture was stirred for 40 minutes. The solvent was removed and the residue was washed with water to give a white solid, which was directly used for the next step.

Workup

  1. customThe solvent was removed
  2. washthe residue was washed with water
  3. customto give a white solid, which

Sources & evidence

ORD record
ord-88f710a5d1d747f79567fda651dbfc6d
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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