Water → {1-Azabicyclo[3.2.1]octan-5-yl}methanol

HRID 1612730Notes

Reaction equation

HRID 1612730 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C([O:14][C:15]([C:17]12[CH2:24][N:21]([CH2:22][CH2:23]1)[CH2:20][CH2:19][CH2:18]2)=O)C.O.[OH-].[Na+]>O1CCCC1>[N:21]12[CH2:24][C:17]([CH2:15][OH:14])([CH2:23][CH2:22]1)[CH2:18][CH2:19][CH2:20]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15663615Ethyl 1-azabicyclo[3.2.1]octane-5-carboxylateHCID 68718528lithium aluminium hydride THF

Product 1

HCID 19795992{1-Azabicyclo[3.2.1]octan-5-yl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) solution of 1.0 N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

Workup

  1. temperaturerefluxed for one hour
  2. temperaturecooled (0° C.)
  3. filtrationthe mixture was filtered through Celite (the solid
  4. washwas washed with tetrahydrofuran) and
  5. concentrationconcentrated in vacuo
  6. customto afford 6.50 g (92%) of viscous, colorless oil, which
  7. temperatureon cooling

Sources & evidence

ORD record
ord-a572a562238e4a30b05c8617107ae343
Source dataset
uspto-grants-1993_03
Patent number
US05190953

Reaction notes

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