Monobenzone → (2S)-2-{2-[4-(Benzyloxy)phenoxy]-1-hydroxyethyl}-1-(tert-butoxycarbonyl)pyrrolidine

HRID 1720508Notes

Reaction equation

HRID 1720508 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]1[O:15][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:14][CH:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[OH:15])=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 7638MonobenzoneHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 57047086(2S)-2-{2-[4-(Benzyloxy)phenoxy]-1-hydroxyethyl}-1-(tert-butoxycarbonyl)pyrrolidineYield 59.1%

Procedure

By the same procedure as in Example 26-B), while using (2S)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (1.50 g) and 4-(benzyloxy)phenol (2.96 g), there was obtained 1.72 g of the title compound.

Sources & evidence

ORD record
ord-5eae28f4bd584fe69cb6419cf358b704
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

Loading…