(+-)-3-Quinuclidinol → HCID 23295014, compound

HRID 1955276Notes

Reaction equation

HRID 1955276 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([Cl:14])=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[CH:17]([OH:23])[CH2:16]2>>[ClH:14].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]([O:23][CH:17]3[CH:18]4[CH2:21][CH2:22][N:15]([CH2:20][CH2:19]4)[CH2:16]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 23295061HCID 23295061, compound

Product 1

HCID 23295014HCID 23295014, compound

Procedure

The title compound was prepared in an analogous manner to that in Example 36. 1-(4-Bromophenyl)cyclobutanecarbonyl chloride, prepared from the compound prepared in Example 10, was refluxed with 3-quinuclidinol overnight. The crude was chromatographed on silica gel using EtOAc-Et3N 90:10 as eluent. The yield was 0.46 g (19%); mp 222-226° C.; 1H NMR (CD3OD) δ 1.73 (m, 2H), 1.82-2.15 (m, 4H), 2.23 (br, 1H), 2.53 (m, 2H), 2.85 (m, 2H), 2.95-3.10 (m, 2H), 3.20-3.35 (m, 3H), 3.66 (m, 1H), 5.06 (m, 1H), 7.25 (d, 2H), 7.50 (d, 2H). Anal. (C18H22BrNO2.HCl) C, H, N.

Workup

  1. customThe crude was chromatographed on silica gel

Sources & evidence

ORD record
ord-5941c00d739c438398d618a5f56f2243
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

Loading…