2-Naphthol → Rac-(2-isopropoxy-5-methanesulfonyl-phenyl)-[3-(naphthalen-2-yloxy)-pyrrolidin-1-yl]-methanone

HRID 1711752Notes

Reaction equation

HRID 1711752 reaction equation
[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][CH:11]([O:14]S(C)(=O)=O)[CH2:10]1)=[O:8])([CH3:3])[CH3:2].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1O>>[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][CH:11]([O:14][C:29]2[CH:28]=[CH:27][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[CH2:10]1)=[O:8])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 86632-NaphtholHCID 58673069Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester

Product 1

HCID 11539733Rac-(2-isopropoxy-5-methanesulfonyl-phenyl)-[3-(naphthalen-2-yloxy)-pyrrolidin-1-yl]-methanoneYield 40%

Procedure

Prepared in analogy to Example 3(c) from rac-methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester (Example 14(a)) and 2-naphthol. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous yellow solid (yield 40%). MS (m/e): 454.5 (M+H+, 100%).

Workup

  1. customThe crude material was purified by reversed phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-ef834a05377f4ef292f682181d8dcb6c
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

Loading…