Allyl bromide → Tert-butyl 4-(4-allyloxyphenyl)-3-hydroxypiperidine-1-carboxylate

HRID 1005065Notes

Reaction equation

HRID 1005065 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)[CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+]>>[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

In an analogous manner to the procedure described in Example 14, by alkylating tert-butyl (3RS,4RS)-3-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate with allyl bromide in the presence of potassium carbonate there was obtained tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-hydroxy-piperidine-1-carboxylate as a colourless solid; m.p.: 113° C. (hexane).

Sources & evidence

ORD record
ord-5922224c7167465b8d44b7fdbf8779d8
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

Loading…