HCID 21906948, compound → HCID 22574499, compound

Temperature

0 °C

To a 0° C. cooled solution tert-butyl 2-(2-sulfanyladamantan-2-yl)acetate (4.1 g, 24.1 mmol) in anhydrous dichloromethane (40 mL) lithium aluminum hydride (1 M solution in THF) (40 mL) was added dropwise over a period of 20 minutes. The reaction mixture was stirred at 0° C. for further 15 minutes and then at room temperature for 30 minutes. The excess LiAlH4 was destroyed by the addition of ethyl acetate. The reaction mixture was then poured over ice cold water, acidified with 1 N HCl and extracted with dichloromethane (2×200 mL). The combined extracts were washed with brine (1×75 mL), dried over sodium sulfate, filtered and solvent evaporated at reduced pressure to give the title compound (3.1 g), mp 68-70° C.; 1H NMR (CDCl3): δ1.16-1.9 (m, 11H), 2.1 (m, 2H), 2.22 (t, J=6.9 Hz, 3H), 2.43 (m, 2H), 3.93 (t, J=6.9 Hz, 2H); 13C NMR (CDCl3): δ26.8, 27.7, 33.2, 33.9, 38.2, 39.1, 43.4, 55.8, 59.4; LRMS (APIMS) (m/z) 230 (M+18) (M+NH4).

1. additionwas added dropwise over a period of 20 minutes
2. waitat room temperature for 30 minutes
3. customThe excess LiAlH4 was destroyed by the addition of ethyl acetate
4. additionThe reaction mixture was then poured over ice cold water
5. extractionextracted with dichloromethane (2×200 mL)
6. washThe combined extracts were washed with brine (1×75 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customsolvent evaporated at reduced pressure

ORD record

ord-11533313ed014f71af4362c4454511bc

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06469065B1