Allyl bromide → 2-Bromomethylnaphthalene

HRID 1005102Notes

Reaction equation

HRID 1005102 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.[CH2:22]([Br:25])[CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:24]([O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]2[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3][CH:2]2[OH:1])=[CH:13][CH:12]=1)[CH:23]=[CH2:22].[Br:25][CH2:22][C:23]1[CH:6]=[CH:7][C:8]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:24]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 21713087(3S,4S)-tert-Butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

Product 2

HCID 703202-BromomethylnaphthaleneHCID 54331732Tert-butyl 4-(4-allyloxyphenyl)-3-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In an analogous manner to that described in Example 44 (e), by alkylating tert-butyl (3RS,4RS)-3-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate [Example 46 (b)] with allyl bromide in the presence of potassium carbonate in acetone there was obtained tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-hydroxy-piperidine-1-carboxylate, alkylation of which with 2-bromomethylnaphthalene in analogy to Example 1 (g) gave tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless resin; MS: 474 (M+H)+.

Sources & evidence

ORD record
ord-e78ba07c3a984792b7e8892fc1c11be3
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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