4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3S)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-one → 2-[(3R)-3-(2-fluoroethoxy)-1-pyrrolidinyl]ethanol

HRID 15078Notes

Reaction equation

HRID 15078 reaction equation
ClC1C=CC(COC2C=CN(C3C=CC([O:22][CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26]4)=CC=3)C(=O)C=2)=NC=1.[F:32][CH2:33][C@@H:34]1CCCN1C(OC(C)(C)C)=O.FCCO[C@@H]1CCN(C(OC(C)(C)C)=O)C1>>[F:32][CH2:33][CH2:34][O:30][C@@H:27]1[CH2:28][CH2:29][N:25]([CH2:24][CH2:23][OH:22])[CH2:26]1

Participants

4

Reactant 3

HCID 589649034-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3S)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-oneHCID 86586409(S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylateHCID 86614896tert-butyl (3R)-3-(2-fluoroethoxy)pyrrolidine-1-carboxylate

Product 1

HCID 866148972-[(3R)-3-(2-fluoroethoxy)-1-pyrrolidinyl]ethanol

Procedure

Steps (2) and (3) of Example 89 were repeated except that tert-butyl (2S)-2-(fluoromethyl)pyrrolidine-1-carboxylate used in the Step (2) was replaced with tert-butyl (3R)-3-(2-fluoroethoxy)pyrrolidine-1-carboxylate, to provide the title compound.

Sources & evidence

ORD record
ord-d32f389d5b4544a1bce23de638792fbd
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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