Water → 1-Azabicyclo[3.3.1]nonan-4-ol

HRID 553431Notes

Reaction equation

HRID 553431 reaction equation
[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[C:4](=[O:10])[CH2:3][CH2:2]2.N1C2C(=CC(C3C=NC(O[C@@H]4[C@H]5CN(CCC5)CC4)=NC=3)=CC=2)C=C1.[BH4-].[Na+].O>CO>[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH:4]([OH:10])[CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67459185HCID 67459185, compound

Product 1

HCID 189861071-Azabicyclo[3.3.1]nonan-4-olYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

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.

Workup

  1. customdoes not exceed 0° C
  2. customthe solvents are evaporated
  3. dissolutionThe remaining solid is dissolved in MTBE/MeOH
  4. filtrationfiltered over hyflo
  5. customthe filtrate is evaporated
  6. customto give 19.28 g of crude product which
  7. customis purified by chromatography over aluminum oxide (400 g, eluent: MTBE/MeOH 95:5 to 80:20)

Sources & evidence

ORD record
ord-66e7debc52624f878cfa2ba7cf860426
Source dataset
uspto-grants-2011_11
Patent number
US08048885B2

Reaction notes

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