Hydrochloric Acid → Tert-butyl 4-amino-4-methylcyclohexylcarbamate hydrochloride

HRID 246652Notes

Reaction equation

HRID 246652 reaction equation
CC(C)(S([NH:6][C:7]1([CH3:21])[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:8]1)=O)C.[ClH:23]>CO.O1CCOCC1>[ClH:23].[NH2:6][C:7]1([CH3:21])[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71280131Tert-butyl 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate

Product 1

HCID 71279525Tert-butyl 4-amino-4-methylcyclohexylcarbamate hydrochlorideYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate (0.2 g, 0.6 mmol) in 100 mL of MeOH was added a saturated solution of HCl (g) in dioxane (0.72 mL). The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was triturated with EtOAc (15 mL), then decanted and dried to give tert-butyl 4-amino-4-methylcyclohexylcarbamate hydrochloride (0.1 g, 63%) as a white solid. MS: (M+H)+=229.2. 1H NMR (300 MHz, CD3OD): δ 3.36 (m, 1H), 1.91-1.66 (m, 9H), 1.40 (s, 9H), 1.18 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with EtOAc (15 mL)
  3. customdecanted
  4. customdried

Sources & evidence

ORD record
ord-aa47209413404b3abcdf0b9f86917b68
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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