3-Quinuclidinol, (-)- → HCID 66959042, compound

HRID 1366718Notes

Reaction equation

HRID 1366718 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([OH:15])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O[C@@H:18]1[CH:23]2C[CH2:25][N:20]([CH2:21][CH2:22]2)[CH2:19]1>C1(C)C=CC=CC=1>[N:20]12[CH2:21][CH2:22][CH:23]([CH2:18][CH2:19]1)[C@@H:1]([O:2][C:3](=[O:16])[C:4]([OH:15])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:25]2

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 66958899HCID 66958899, compound

Product 1

HCID 66959042HCID 66959042, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.7 g of 2-Hydroxy-2-thien-2-ylheptanoic acid methyl ester (Intermediate I-9) (0.011 mol) were dissolved in 70 ml of toluene. To this solution were added 1.63 g (0.0128 mol) of (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane and 0.18 g (0.0045 mol) of HNa (60% dispersion in mineral oil). The mixture was refluxed with continuous removal of distillate with replacement with fresh toluene when necessary for 1 hour. The cooled mixture was extracted with 1N HCl acid, the aqueous layer washed with ether, basified with K2CO3 and extracted with CHCl3. The organic layer was washed with water, dried over MgSO4 and evaporated. The yield was 2.85 g (76%) of the title product as a mixture of diastereomers, structure confirmed by 1H-NMR.

Workup

  1. extractionThe cooled mixture was extracted with 1N HCl acid
  2. washthe aqueous layer washed with ether
  3. extractionextracted with CHCl3
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additionThe yield was 2.85 g (76%) of the title product as a mixture of diastereomers, structure

Sources & evidence

ORD record
ord-a31b34f2614246e29c4fb2336fd6fe7c
Source dataset
uspto-grants-2011_02
Patent number
US07893087B2

Reaction notes

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