Cycloheptanol → HCID 58495535, compound

Temperature

0 °C

Add 6-chloro-pyridin-3-ol (2 g, 15.4 mmol), cycloheptanol (1.93 g, 17 mmol), tri-n-butylphosphine (4.67 mL, 19.3 mmol), and ADDP (4.87 g, 19.3 mmol) to THF (60 mL) at 0° C. under a nitrogen atmosphere. Stir the mixture at 0° C. for 1 h and at room temperature for 12 h. Dilute with EtOAc (50 mL), add water (50 mL) and separate the layers. Extract the aqueous layer with EtOAc (4×30 mL). Wash the combined organic extracts with water (30 mL) and brine (20 mL). Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 1:1 gradient over 1.25 h, 80 mL/min) to obtain the desired intermediate as a colorless oil (2.36 g, 68%). MS (APCI+) m/z: 226 (M H)+.

1. waitat room temperature for 12 h
2. customseparate the layers
3. extractionExtract the aqueous layer with EtOAc (4×30 mL)
4. washWash the combined organic extracts with water (30 mL) and brine (20 mL)
5. dry with materialDry the organic phase over Na2SO4
6. filtrationfilter
7. concentrationconcentrate in vacuo
8. customPurify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge)
9. washeluting with hexane/EtOAc (1:0 to 1:1 gradient over 1.25 h, 80 mL/min)

ORD record

ord-5b4a7a315f004699897c6c55e28fc707

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680091B2