N-Boc-hexahydro-1H-azepin-4-one → tert-Butyl 4-hydroxyazepane-1-carboxylate

A solution of tert-butyl 4-oxoazepane-1-carboxylate (0.60 g, 2.81 mmol), in MeOH (11 mL) was cooled to 0° C. NaBH4 (0.266 g, 7.03 mmol) was added and the mixture was slowly warmed to ambient temperature where the reaction stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in EtOAc (20 mL) and saturated aqueous NH4Cl solution (20 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2×10 mL). The combined organic extracts were washed with brine and dried over Na2SO4, then filtered and concentrated. The product was isolated as a thick colorless oil that solidified overnight to a white solid.

1. concentrationThe mixture was concentrated in vacuo
2. customThe layers were separated
3. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe product was isolated as a thick colorless oil that solidified overnight to a white solid

ORD record

ord-3e07ac8c1c3b4eb0a721f4036f30987d

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575145B2