Hydrochloric Acid → L-alpha-Amino-omega-methyl-1-caprolactam

HRID 1366610Notes

Reaction equation

HRID 1366610 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].Cl>O1CCOCC1>[NH2:9][C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][N:2]([CH3:1])[C:3]1=[O:17]

Participants

4

Reactant 2

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

Product 1

HCID 14003483L-alpha-Amino-omega-methyl-1-caprolactam

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,1-dimethylethyl [(3S)-1-methyl-2-oxohexahydro-1H-azepin-3-yl]carbamate (470 mg, 1.9 mmol) in dioxane (5 mL) was added HCl (4.8 mL, 19 mmol, 4M in dioxane), and the reaction was stirred overnight. Evaporation of the solvent gave a quantitative yield of (3S)-3-amino-1-methylhexahydro-2H-azepin-2-one. LCMS: (M+H)+: 143.1.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5b462b65c8fc4ad9aafea92bd1704200
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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