3-Methylidenequinuclidinol → HCID 23295018, compound

HRID 1955278Notes

Reaction equation

HRID 1955278 reaction equation
[ClH:1].[C:2]1([C:8]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]=[C:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH:17]1O>C(Cl)Cl>[ClH:1].[C:2]1([C:8]2([C:12]([O:14][CH:17]3[C:16](=[CH2:15])[CH:21]4[CH2:22][CH2:23][N:18]3[CH2:19][CH2:20]4)=[O:13])[CH2:9][CH2:10][CH2:11]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 232950493-MethylidenequinuclidinolHCID 702761261-Phenylcyclobutanecarboxylate hydrochloride

Product 1

HCID 23295018HCID 23295018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-phenylcyclobutanecarboxylate hydrochloride with 3-methylidenequinuclidinol. The esterification was carried out in CH2Cl2. The crude was chromatographed on silica gel using toluene-Et3N 88:12 as eluent. The yield was 0.07 g (9%); mp 155-157° C.; 1H NMR (CDCl3) δ 1.80-2.10 (m, 7H), 2.25 (m, 1H), 2.52 (m, 2H), 2.76 (m, 3H), 3.18 (m, 5H), 4.09 (m, 2H), 7.29 (m, 5H), 12.2 (br, 1H). Anal. (C19H25NO2.HCl) H, N; C: calcd, 67.94; found, 67.25.

Workup

  1. customThe crude was chromatographed on silica gel

Sources & evidence

ORD record
ord-87a51294d0aa43888f8d61e739d32ec5
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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