Borane;tetrahydrofuran → HCID 57440699, compound

Temperature

85 °C

Borane-tetrahydrofuran complex (1M in THF) (3 mL, 3 mmol) was added dropwise to the product from example 45 (0.33 g, 1.18 mmol) in dry THF (4 mL) under an atmosphere of nitrogen. The reaction mixture was heated at 85° C. for 3 hours then cooled and quenched by the addition of methanol (1 mL). The reaction mixture was then concentrated in vacuo and the residue suspended in 6N HCl (aq) (110 mL) and heated to 60° C. for 1.5 hours. The reaction mixture was cooled and extracted with diethyl ether (2×10 mL). The aqueous layer was rendered basic (pH 9-10) by addition of solid potassium carbonate before re-extracting with dichloromethane (2×15 mL). The dichloromethane extracts were dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the crude products as a clear oil.

1. temperaturethen cooled
2. customquenched by the addition of methanol (1 mL)
3. concentrationThe reaction mixture was then concentrated in vacuo
4. temperatureheated to 60° C. for 1.5 hours
5. temperatureThe reaction mixture was cooled
6. extractionextracted with diethyl ether (2×10 mL)
7. additionby addition of solid potassium carbonate
8. extractionbefore re-extracting with dichloromethane (2×15 mL)
9. dry with materialThe dichloromethane extracts were dried over anhydrous magnesium sulphate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-dfb07a8229654beb87e6495d6ef23943

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902188B2