2-Chloromethyl-1,4-dimethoxy-naphthalene → tert-butyl (3'RS,4'RS)-3'-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-6-methylsulfanyl-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridine-1'-carboxylate

HRID 1005204Notes

Reaction equation

HRID 1005204 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:9]=[N:10][C:11]([S:14][CH3:15])=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3]1.Cl[CH2:24][C:25]1[CH:34]=[C:33]([O:35][CH3:36])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]=1[O:37][CH3:38]>>[CH3:38][O:37][C:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]([O:35][CH3:36])=[CH:34][C:25]=1[CH2:24][O:1][CH:2]1[CH:7]([C:8]2[CH:9]=[N:10][C:11]([S:14][CH3:15])=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3]1

Participants

3

Reactant 2

HCID 148548022-Chloromethyl-1,4-dimethoxy-naphthaleneHCID 54552362tert-butyl (3'RS,4'RS)-3'-hydroxy-6-methylsulfanyl-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridine-1'-carboxylate

Product 1

HCID 53795634tert-butyl (3'RS,4'RS)-3'-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-6-methylsulfanyl-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridine-1'-carboxylate

Procedure

In an analogous manner to that described in Example 125 (g), from tert-butyl (3'RS,4'RS)-3'-hydroxy-6-methylsulphanyl-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridine-1'-carboxylate by alkylation with 2-chloromethyl-1,4-dimethoxy-naphthalene [J. Amer. Chem. Soc. 64, 2657 (1942)] there was obtained tert-butyl (3'RS,4'RS)-3'-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-6-methylsulphanyl-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridine-1'-carboxylate in the form of a colourless solid; MS: 526 (M+H)+.

Sources & evidence

ORD record
ord-149fed7ed2744b5bbf819e4408dd48ad
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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