Sodium hydride → HCID 67219952, compound

HRID 843419Notes

Reaction equation

HRID 843419 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([O:14][CH2:15][C@H:16]2[CH2:18][O:17]2)[C@H:11]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]#[N:37])=[CH:21][CH:20]=2)[C@@H:10]([O:38][CH2:39][C:40]2[CH:49]=[C:48]([O:50][CH3:51])[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>COCCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@H:10]([O:38][CH2:39][C:40]2[CH:49]=[C:48]([O:50][CH3:51])[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=2)[C@@H:11]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]#[N:37])=[CH:23][CH:24]=2)[C@H:12]([O:14][CH2:15][C@H:16]([OH:17])[CH2:18][O:17][CH2:16][CH2:15][O:14][CH3:12])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57271843HCID 57271843, compound

Product 1

HCID 67219952HCID 67219952, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

In analogy to the procedure described in example 1 (k) the (3R,4R,5S)-4-[4-[3-(2-cyano-phenoxy)-propoxy]-phenyl]-3-(4-methoxy-naphthalen-2-ylmethoxy)-5-[(2R)-oxiranylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester was treated with sodium 2-methoxy-ethylate (prepared from 2-methoxy-ethanol and sodium hydride) to give the (3S,4R,5R)-4-[4-[3-(2-cyano-phenoxy)-propoxy]-phenyl]-3-[(2R)-2-hydroxy-3-(2-methoxy-ethoxy)-propoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as colorless oil; MS: 771 (M+H)+.

Sources & evidence

ORD record
ord-fb54f39c3ef14263ae8c58a98051445f
Source dataset
uspto-grants-2002_04
Patent number
US06376672B1

Reaction notes

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