Allyl bromide → HCID 11209475, compound

HRID 1794115Notes

Reaction equation

HRID 1794115 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:11](Br)[CH:12]=[CH2:13].Cl[C:16]([N:18]1[C@H:23]([CH3:24])[CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][C@@H:19]1[CH3:32])=[O:17]>>[CH3:24][C@H:23]1[CH2:22][NH:21][CH2:20][C@@H:19]([CH3:32])[N:18]1[C:16]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([O:10][CH2:13][CH:12]=[CH2:11])[CH:8]=[CH:9][C:2]=1[F:1])=[O:17]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 11209475HCID 11209475, compound

Procedure

2-Fluoro-5-(2-propenyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, allyl bromide and 1-chlorocarbonyl-cis-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the methods described for Examples 54 and 121 to give the product as a yellow oil (8.4%); HPLC (XTERRA, 50/80, 220 nm) 95.7% (2.87 min); NMR δH (400 MHz, DMSO-d6) 1.183(6H, d, J 6.5 Hz), 2.673(4H, m), 3.294(2H, bs), 3.910(2H, m), 4.572(2H, m), 5.078(2H, s), 5.252(1H, m), 5.371(1H, m), 6.022(1H, m), 6.948(2H, m) and 7.138(1H, t, J 9.5 Hz).

Sources & evidence

ORD record
ord-edb3e0430c29491093c2eaea19629543
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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