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

HRID 869658Notes

Reaction equation

HRID 869658 reaction equation
[CH2:1]([O:8][CH2:9][O:10][C@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:13]([CH2:23][OH:24])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:26]1[C:27]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:28][CH:29]=[CH:30][CH:31]=1.ClC1C=C(O)C=NC=1>>[CH2:1]([O:8][CH2:9][O:10][C@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@@H:13]([CH2:23][O:24][C:26]2[C:27]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5823053-Hydroxy-5-chloropyridineHCID 15080989Ethyl 3-hydroxypicolinateHCID 66961725(2R,4R)-tert-butyl 4-(benzyloxymethoxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 66962068ethyl 3-(((2R,4R)-4-(benzyloxymethoxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methoxy)picolinate

Procedure

The title compound was prepared according to the procedure described in Step 1 of EXAMPLE 29 using (2R,4R)-tert-butyl 4-(benzyloxymethoxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (EXAMPLE 79 Step 2) and ethyl 3-hydroxypicolinate instead of (R)-pyrrolidin-2-ylmethanol and 5-chloropyridin-3-ol.

Sources & evidence

ORD record
ord-3f9705338f904d2185b0f25ba8053b6d
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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