Acetone → HCID 45088427, compound

N-Boc-hexahydro-1H-azepine-4-one (3.00 g, 14.1 mmol) was dissolved in DCM (50 mL), TFA (15 mL) was added and the reaction mixture was stirred for 2 h. The solvents were removed in vacuo and the residue partitioned between DCM (500 mL) and sat aq Na2CO3 (500 mL). The aq fraction was extracted with DCM (2×250 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DCM (50 mL) and acetone (10 mL) and NaBH(OAc)3 (2.18 g, 141 mmol) were added. The reaction mixture was stirred for 18 h, diluted with DCM (200 mL) and quenched with sat aq Na2CO3 (150 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo to give the crude title compound (2.18 g) as a brown liquid. LCMS (ES+): 156.2 [MH]+.

1. customThe solvents were removed in vacuo
2. customthe residue partitioned between DCM (500 mL)
3. extractionThe aq fraction was extracted with DCM (2×250 mL)
4. dry with materialthe combined organic fractions were dried (MgSO4)
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in DCM (50 mL)
7. stirringThe reaction mixture was stirred for 18 h
8. customquenched with sat aq Na2CO3 (150 mL)
9. dry with materialThe organic fraction was dried (MgSO4)
10. concentrationconcentrated in vacuo

ORD record

ord-62f09b7f64c448ce9f4f280286152607

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353086B2