2-Chloromethyl-1,4-dimethoxy-naphthalene → tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

HRID 1005247Notes

Reaction equation

HRID 1005247 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]2[OH:24])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].Cl[CH2:26][C:27]1[CH:36]=[C:35]([O:37][CH3:38])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]=1[O:39][CH3:40]>>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]2[O:24][CH2:26][C:27]2[CH:36]=[C:35]([O:37][CH3:38])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[O:39][CH3:40])=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 148548022-Chloromethyl-1,4-dimethoxy-naphthaleneHCID 54331732Tert-butyl 4-(4-allyloxyphenyl)-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 53648544tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Procedure

(a) In an analogous manner to that described in Example 1 (g), by alkylating tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-hydroxy-piperidine-1-carboxylate [Example 86 (b)] with 2-chloromethyl-1,4-dimethoxy-naphthalene [J.Org.Chem. (1983), 48(19),3265-3268) there was obtained tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a pale yellow solid; MS: 534 (M+H)+.

Sources & evidence

ORD record
ord-9bcc4534e7f8469fbce9ae13aafe017d
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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