Dimethyl Sulfoxide → 3,5-Dimethyltricyclo[3.3.1.1~3,7~]decane-1-carbaldehyde

Temperature

-78 °C

To a solution of DMSO (4 mL, 57.7 mmol) in DCM (125 mL) under nitrogen at −78° C. was added dropwise oxalyl chloride (2.0 M in DCM, 18.75 mL, 37.5 mmol) over 30 min. After final addition the reaction mixture was stirred at −78° C. for 30 min. With the reaction mixture still at −78° C. , a solution of crude (3,5-dimethyladamant-1-yl)methanol from above in DCM (50 mL) was added dropwise over 20 min. After stirring the reaction at −78° C. for 2 h, Et3N (15 mL) was added slowly over 10 min and the reaction was stirred for 30 min at −78° C. Saturated NaH2PO4 (15 mL) was added followed by water (150 mL), and the reaction was then warmed to rt. The DCM layer was separated, washed twice with 1N HCl and sat'd NaHCO3, dried over MgSO4, filtered and concentrated to give the step 1 compound, 3,5-dimethyladamantane-1-carboxaldehyde (5.58 g).

1. additionAfter final addition the reaction mixture
2. stirringAfter stirring
3. customthe reaction at −78° C. for 2 h
4. stirringthe reaction was stirred for 30 min at −78° C
5. temperaturethe reaction was then warmed to rt
6. customThe DCM layer was separated
7. washwashed twice with 1N HCl
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-c80187ba262c465c822b690e7c5ebff6

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06995183B2