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

HRID 529503Notes

Reaction equation

HRID 529503 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:15]C(=O)OC(C)(C)C)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:24].O1CCOCC1>C(Cl)Cl>[ClH:24].[NH2:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68311020(S)-tert-butyl 1-benzyl-2-oxoazepan-3-ylcarbamate

Product 1

HCID 68292429(S)-3-amino-1-benzylazepan-2-one hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-benzyl-2-oxoazepan-3-ylcarbamate (340 mg, 1.07 mmol) in DCM (5 mL) was added solution of 4 M HCl in dioxane (0.243 mL, 0.971 mmol) at rt under argon. The reaction was allowed to stir at rt for 5 hr. The reaction mixture was concentrated and dried under vacuum to give (S)-3-amino-1-benzylazepan-2-one hydrochloride (210 mg, 0.962 mmol, 99% yield) as a white solid. Anal. Calcd. for C13H18N2O m/z 218.3. found: 219.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-6e5d0229b64441da87ce378584bf17d1
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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