Diisobutylaluminum hydride → 3-(Dibenzylamino)-2,2-difluoropropan-1-ol

At −78° C. to a solution of ethyl 3-(dibenzylamino)-2,2-difluoropropanoate (1.19 g, 3.5 mmol) in THF (20 mL) was added DIBAL-H (15 mL, 1.0 M in hexane, 15 mmol) dropwise. The temperature was maintained at below −70° C. during the addition. After the addition, the acetone-dry ice bath was removed and the reaction mixture was allowed to warm up to room temperature and stirred for 18 h. Celite was added to the reaction mixture, followed by the slow addition of H2O (5 mL), 2 N NaOH (5 mL) and H2O (5 mL). The reaction mixture was filtered, concentrated in vacuo and purified by ISCO chromatography to give 3-(dibenzylamino)-2,2-difluoropropan-1-ol as a colorless oil (810 mg, 80% yield) LCMS: RT=2.48 min [M+H] 292.15 (LCMS Method 1).

1. temperatureThe temperature was maintained at below −70° C. during the addition
2. additionAfter the addition
3. customthe acetone-dry ice bath was removed
4. additionCelite was added to the reaction mixture
5. additionfollowed by the slow addition of H2O (5 mL), 2 N NaOH (5 mL) and H2O (5 mL)
6. filtrationThe reaction mixture was filtered
7. concentrationconcentrated in vacuo
8. custompurified by ISCO chromatography

ORD record

ord-369958fb779b4000beec641ee1507c80

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888376B2