Hydrochloric Acid → (3S)-3-amino-1-methyl-1,3,4,7-tetrahydro-2H-azepin-2-one

HRID 1366444Notes

Reaction equation

HRID 1366444 reaction equation
[CH3:1][N:2]1[CH2:8][CH:7]=[CH:6][CH2:5][C@H:4]([NH:9]C(=O)OC(C)(C)C)[C:3]1=[O:17].Cl>C(Cl)Cl>[NH2:9][C@H:4]1[CH2:5][CH:6]=[CH:7][CH2:8][N:2]([CH3:1])[C:3]1=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866369401,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

Product 1

HCID 66936420(3S)-3-amino-1-methyl-1,3,4,7-tetrahydro-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (0.6 g, 2.5 mmol) in DCM (4 mL) was added HCl (6.2 mL, 25 mmol, 4M in dioxane) and the resulting mixture was stirred for 12 hours. Removal of the solvents under reduced pressure yielded (3S)-3-amino-1-methyl-1,3,4,7-tetrahydro-2H-azepin-2-one.HCl (500 mg, quantitative). LCMS: (M+H)+: not detected.

Workup

  1. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-2ffb76e3d5d646eea05d5d5c929aff43
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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