Allyl bromide → HCID 67219970, compound

HRID 1838738Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:28][CH:27]=2)[CH:10]([CH2:44][OH:45])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:46](Br)[CH:47]=[CH2:48]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:11]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:30][CH:31]=2)[CH:10]([CH2:44][O:45][CH2:48][CH:47]=[CH2:46])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 15546932HCID 15546932, compound

Product 1

HCID 67219970HCID 67219970, compound

Procedure

In an analogous manner to that described in Example 13 (g), by alkylating (3SR,4RS,5RS)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-hydroxymethyl-5-(naphthalen-2ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester [WO 9709311, Example 148 (h)] with allylbromide there was obtained (3SR,4RS,5RS)-3-allyloxymethyl-4-[4-(3-benzyloxy-propoxy)-phenyl]-5-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as a colorless solid; MS: 652 (M+H)+.

Sources & evidence

ORD record: ord-700b8add38464a568fcc1adf4239805d
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673931B2

Reaction notes

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