Reaction #640613

Reaction equation

(4S,5R)-4-[5-(1H-Indol-5-yl)-pyrimidin-2-yloxy]-1-aza-bicyclo[3.3.1]nonane 1-Aza-bicyclo[3.3.1]nonan-4-one

NaBH4

Water

→

(4SR,5RS)-1-aza-bicyclo[3.3.1]nonan-4-ol

Yield 91.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Otherdoes not exceed 0° C
2. 2
   Otherthe solvents are evaporated
3. 3
   workup.DISSOLUTIONThe remaining solid is dissolved in MTBE/MeOH
4. 4
   Filtrationfiltered over hyflo
5. 5
   Otherthe filtrate is evaporated
6. 6
   Otherto give 19.28 g of crude product which
7. 7
   Otheris purified by chromatography over aluminum oxide (400 g, eluent: MTBE/MeOH 95:5 to 80:20)

Procedure

(4S,5R)-4-[5-(1H-Indol-5-yl)-pyrimidin-2-yloxy]-1-aza-bicyclo[3.3.1]nonane 1-Aza-bicyclo[3.3.1]nonan-4-one (11.92 g, 85.6 mmol) is dissolved in 160 ml MeOH and cooled to −10° C. NaBH4 (1.69 g, 42.9 mmol)) is added portionwise so that the inner temperature does not exceed 0° C. The reaction mixture is stirred at −10° C. for 1 h. Water is added and the solvents are evaporated. The remaining solid is dissolved in MTBE/MeOH, filtered over hyflo and the filtrate is evaporated to give 19.28 g of crude product which is purified by chromatography over aluminum oxide (400 g, eluent: MTBE/MeOH 95:5 to 80:20) to give 10.96 g (91%) (4SR,5RS)-1-aza-bicyclo[3.3.1]nonan-4-ol.

Source