Hydrochloric Acid → Tert-butyl 3-amino-3-methylcyclobutylcarbamate hydrochloride

HRID 246668Notes

Reaction equation

HRID 246668 reaction equation
CC(C)(S([NH:6][C:7]1([CH3:19])[CH2:10][CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8]1)=O)C.[ClH:21]>CO.O1CCOCC1>[ClH:21].[NH2:6][C:7]1([CH3:19])[CH2:10][CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71280661Tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-methylcyclobutylcarbamate

Product 1

HCID 71280568Tert-butyl 3-amino-3-methylcyclobutylcarbamate hydrochlorideYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-methylcyclobutylcarbamate (0.45 g, 1.48 mmol) in 150 mL of MeOH was added 2N HCl in dioxane (1.8 mL). The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was triturated with EtOAc, then decanted and dried to give tert-butyl 3-amino-3-methylcyclobutylcarbamate hydrochloride (0.22 g, 63%) as a white solid. MS: (M+H)+=201.2; 1H NMR (300 MHz, DMSO): δ 2.24-2.22 (m, 1H), 1.43-1.383 (m, 13H), 1.10 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-e678869c937c4fa4814edcac208e18ae
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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