3-Hydroxy-5-chloropyridine → ethyl 3-(((2R,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidin-2-yl)methoxy)picolinate

HRID 869664Notes

Reaction equation

HRID 869664 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:11]([CH2:21][OH:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:24]1[C:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=1.ClC1C=C(O)C=NC=1>>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][C@@H:11]1[CH2:21][O:22][C:24]1[C:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 5823053-Hydroxy-5-chloropyridineHCID 15080989Ethyl 3-hydroxypicolinateHCID 66962096tert-butyl (2R,4S)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 66962085ethyl 3-(((2R,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidin-2-yl)methoxy)picolinate

Procedure

The title compound was prepared according to the procedure described in Step 1 of EXAMPLE 29 using (2R,4S)-tert-butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (PCT Int. Appl., WO2009026197) and ethyl 3-hydroxypicolinate instead of (R)-pyrrolidin-2-ylmethanol and 5-chloropyridin-3-ol.

Sources & evidence

ORD record
ord-4f561649bc004db2a0bcd919af6fd065
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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