3-Quinuclidinol, (-)- → 2-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester

HRID 1360613Notes

Reaction equation

HRID 1360613 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[OH:5].O[C@@H:19]1[CH:24]2C[CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1>C1(C)C=CC=CC=1>[N:21]12[CH2:22][CH2:23][CH:24]([CH2:19][CH2:20]1)[C@@H:1]([O:2][C:3](=[O:17])[C:4]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[OH:5])[CH2:26]2

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 669589942-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester

Product 1

HCID 669591572-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared using the same method as for Intermediate I-1, but from 13.73 g (0.057 mol) of 2-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester (Intermediate I-11) dissolved in 350 ml of toluene, 8.6 g (0.067 mol) of (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane and 1.37 g (0.0342 mol) of HNa (60% dispersion in mineral oil). The oil obtained (10.33 g) was purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 97:3:0.3. Appropriate fractions were combined and evaporated to obtain the two diastereomers: I-4a and I-4b.

Workup

  1. customPrepared
  2. customThe oil obtained (10.33 g)
  3. customwas purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 97:3:0.3
  4. customevaporated
  5. customto obtain the two diastereomers

Sources & evidence

ORD record
ord-baf9a1a7a4574d65accd9f191f9a0d80
Source dataset
uspto-grants-2011_02
Patent number
US07879874B2

Reaction notes

Loading…