Reaction #52236

Reaction equation

1-Boc-isonipecotic acid

BH3-THF

→

l-Boc-piperidine-4-methanol

Yield 85.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureto warm to room temperature for 12 h
2. 2
   OtherThe mixture was carefully quenched with water
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   ExtractionThe water layer was extracted with ethyl acetate
5. 5
   Washwashed with brine
6. 6
   Dryingdried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

1-Boc-isonipecotic acid (10.0 g, 214 mmol) was dissolved in THF (400 mL) and cooled to 0° C. A solution of BH3-THF (180 mL, 1 N in THF, 180 mmol) was added slowly. The mixture stirred for 1 h at 0° C. and was allowed to warm to room temperature for 12 h. The mixture was carefully quenched with water and diluted with ethyl acetate. The water layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated to provide l-Boc-piperidine-4-methanol (7.98 g, 85%) as a white solid.

Source