(+-)-3-Quinuclidinol → HCID 23295058, compound

HRID 1955273Notes

Reaction equation

HRID 1955273 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13]([Cl:15])=[O:14])[CH2:12][CH2:11][CH2:10]1.[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[CH:18]([OH:24])[CH2:17]2>>[ClH:15].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13]([O:24][CH:18]2[CH:19]3[CH2:22][CH2:23][N:16]([CH2:21][CH2:20]3)[CH2:17]2)=[O:14])[CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 23295067HCID 23295067, compound

Product 1

HCID 23295058HCID 23295058, compound

Procedure

The title compound was prepared in an analogous manner to that in Example 36. 1-(2-Methoxyphenyl)cyclobutanecarbonyl chloride, prepared from the compound prepared in Example 17, was reacted with 3-quinuclidinol at 80° C. for 25 h. A crude product was obtained which was rechromatographed on a reverse-phase PEP RPC HR 30/26 column using a gradient of 25-50% CH3CN with 0.1% TFA. The yield was 0.2 g (6%); mp 121-123° C.; 1H NMR (D2C) δ 1.70-1.85 (m, 2H), 1.93-2.03 (m, 2H), 2.10 (m, 1H), 2.19 (m, 1H), 2.39 (m, 1H), 2.54 (m, 2H), 2.77 (m, 2H), 3.01 (q, 1H), 3.18 (d, 1H), 3.28-3.37 (m, 3H), 3.75 (m, 1H), 3.85 (s, 3H), 5.24 (m, 1H), 7.13 (d, 1H), 7.17 (t, 1H), 7.45 (t, 1H), 7.53 (d, 1H). Anal. (C19H25NO2.HCl.H2O) C, H, N.

Sources & evidence

ORD record
ord-fad236bcc9fa42ca80e37cd4c0edf888
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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