Hydrochloric Acid → (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl N-(2-amino-2-methylcyclopentyl)carbamate hydrochloride

HRID 1750506Notes

Reaction equation

HRID 1750506 reaction equation
C(OC([NH:8][C:9]1([CH3:28])[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:27])[O:16][C@@H:17]1[CH2:22][C@H:21]([CH3:23])[CH2:20][CH2:19][C@H:18]1[CH:24]([CH3:26])[CH3:25])=O)(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[NH2:8][C:9]1([CH3:28])[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:27])[O:16][C@@H:17]1[CH2:22][C@H:21]([CH3:23])[CH2:20][CH2:19][C@H:18]1[CH:24]([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308072(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl N-(2-{[(tert-butoxy)carbonyl]amino}-2-methylcyclopentyl)carbamate

Product 1

HCID 118308291(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl N-(2-amino-2-methylcyclopentyl)carbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl N-(2-{[(tert-butoxy)carbonyl]amino}-2-methylcyclopentyl)carbamate (6.12 g, 15.43 mmol) in 1,4-dioxane (35 ml) was added HCl in 1,4-dioxane (4 M, 38.6 ml, 154 mmol). The reaction mixture was stirred at room temperature overnight, concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-6876f2e25f1249778ea61b7a3685b1ea
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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