(+-)-3-Quinuclidinol → HCID 23295042, compound

HRID 1955272Notes

Reaction equation

HRID 1955272 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[CH3:10][C:11]1[CH:12]=[C:13]([C:17]2([C:21]([Cl:23])=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1>>[ClH:23].[CH3:10][C:11]1[CH:12]=[C:13]([C:17]2([C:21]([O:9][CH:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-Quinuclidinol2×HCID 23295044HCID 23295044, compound

Product 1

HCID 23295042HCID 23295042, compound

Procedure

The title compound was prepared in an analogous manner to that in Example 36 from the compound prepared in Example 16 and 3-quinuclidinol. 1-(3-Methylphenyl)cyclobutanecarbonyl chloride was reacted with 3-quinuclidinol at room temperature for 15 min. The eluent was evaporated and the residue was partitioned beween Et2O and NaOH. The organic layer was extracted with 3 M HCl that was basidified and extracted with Et2O. HCl (g)/Et2O was then added whereby the product crystallized to yield 0.25 g (53%); mp 196.5-198° C.; 1H NMR (CDCl3) δ 1.51 (m, 2H), 1.76-2.20 (m, 5H), 2.32 (s, 3H), 2.51 (m, 2H), 2.70-2.80 (m, 3H), 3.03 (d, 1H), 3.24 (m, 3H), 3.52 (m, 1H), 5.00 (m, 1H), 7.05-7.30 (m, 4H)1 12.31 (bs, 1H). Anal. (C19H25NO2.HCl) C, H, N, Cl.

Workup

  1. customThe eluent was evaporated
  2. customthe residue was partitioned beween Et2O and NaOH
  3. extractionThe organic layer was extracted with 3 M HCl that
  4. extractionextracted with Et2O
  5. additionHCl (g)/Et2O was then added whereby the product
  6. customcrystallized
  7. customto yield 0.25 g (53%)

Sources & evidence

ORD record
ord-aa3e4a3877be49d1b008faba84529fd9
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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