Hydrochloric Acid → (3S)-3-amino-1-methylazepan-2-one hydrochloride

HRID 912455Notes

Reaction equation

HRID 912455 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]([NH:9]C(=O)OC(C)(C)C)[C:3]1=[O:17].[ClH:18].O1CCOCC1>ClCCl>[ClH:18].[NH2:9][C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][N:2]([CH3:1])[C:3]1=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 60110341(S)-tert-butyl 1-methyl-2-oxoazepan-3-ylcarbamate

Product 1

HCID 67416248(3S)-3-amino-1-methylazepan-2-one hydrochlorideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-methyl-2-oxoazepan-3-ylcarbamate (prepared according to Example 14; 0.152 g, 0.627 mmol) in dichloromethane (2 mL) was added 4M hydrogen chloride in dioxane (2 mL, 8 mmol), and the reaction mixture was allowed to stir overnight. The reaction mixture was concentrated to yield (S)-3-amino-1-methylazepan-2-one hydrochloride (0.112 g, 99.9% yield) which was taken on to the next step.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-43fee2b892c6427a9145b25bc553d2bb
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

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