Potassium Carbonate → 2-Bromomethylnaphthalene

HRID 1005107Notes

Reaction equation

HRID 1005107 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.[Br:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:34](=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:27]([O:26][CH2:25][CH2:24][CH2:23][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)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Br:22][CH2:23][C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 21713087(3S,4S)-tert-Butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

Product 2

HCID 703202-BromomethylnaphthaleneHCID 54071872HCID 54071872, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

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 benzyl 3-bromopropyl ether in the presence of potassium carbonate in butan-2-one there was obtained tert-butyl (3RS,4RS)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-hydroxy-piperidine-1-carboxylate, alkylation of which with 2-bromomethyl-naphthalene analogously to Example 1 (g) gave tert-butyl (3RS,4RS)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless oil; MS: 582 (M+H)+.

Sources & evidence

ORD record
ord-0916005f4ef44100a3934a10387ca723
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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