(S)-(-)-N-Boc-prolinol → 4-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(2S)-2-pyrrolidinyl]methoxy}phenyl)-1H-pyridin-2-one

HRID 15085

Reaction equation

HRID 15085 reaction equation
O[C@H:2]1[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.OC[C@@H]1CCCN1C(OC(C)(C)C)=O.[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][N:40]([C:43]3[CH:48]=[CH:47][C:46]([O:49][C@@H:50]4CCN(C(OC(C)(C)C)=O)C4)=[CH:45][CH:44]=3)[C:39](=[O:62])[CH:38]=2)=[N:33][CH:34]=1>>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][N:40]([C:43]3[CH:44]=[CH:45][C:46]([O:49][CH2:50][C@@H:3]4[CH2:2][CH2:6][CH2:5][NH:4]4)=[CH:47][CH:48]=3)[C:39](=[O:62])[CH:38]=2)=[N:33][CH:34]=1

Participants

4

Reactant 3

HCID 643448(S)-(-)-N-Boc-prolinolHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 589649934-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one

Product 1

HCID 589649524-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(2S)-2-pyrrolidinyl]methoxy}phenyl)-1H-pyridin-2-one

Procedure

Example 120 was repeated except that tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate was replaced with tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate. The resulting compound was used in placed of 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one which was used in Example 121. Otherwise repeating Example 121, the title compound was obtained.

Sources & evidence

ORD record
ord-b026a47d554941dc974fd4033aa855c2
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

Loading…