(+-)-3-Quinuclidinol → HCID 23294910, compound

HRID 1955277Notes

Reaction equation

HRID 1955277 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:14]([Cl:16])=[O:15])[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[CH:19]([OH:25])[CH2:18]2>C(Cl)Cl>[ClH:16].[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:14]([O:25][CH:19]3[CH:20]4[CH2:23][CH2:24][N:17]([CH2:22][CH2:21]4)[CH2:18]3)=[O:15])[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 23294949Cyclobutanecarbonyl chloride, 1-(3-nitrophenyl)-

Product 1

HCID 23294910HCID 23294910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in an analogous manner to that in Example 36. 1-(3-Nitrophenyl)cyclobutanecarbonyl chloride, prepared from the compound prepared in Example 33, was reacted with 3-quinuclidinol in CH2Cl2 for 2 h. The crude was chromatographed on silica gel using EtOAc-Et3N 90:10 as eluent. The yield was 0.4 g (26%); mp 191-192° C.; 1H NMR (CD3OD) δ 1.73-2.29 (m, 7H), 2.62 (m, 2H), 2.94 (m, 2H), 3.02-3.36 (m, 5H), 3.65-3.75 (m, 1H), 5.10 (m, 1H), 7.60-7.66 (m, 1H), 7.74-7.78 (m, 1H), 8.13-8.18 (m, 2H). Anal. (C18H22N2O4.HCl) C, H, N.

Workup

  1. customThe crude was chromatographed on silica gel

Sources & evidence

ORD record
ord-cce5c2187c344f2da17bd82739fdcee3
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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