Allyl bromide → HCID 69141786, compound

HRID 1794107Notes

Reaction equation

HRID 1794107 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][OH:5].[CH2:12](Br)[CH:13]=[CH2:14].Cl[C:17]([N:19]1[C@H:24]([CH3:25])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][C@@H:20]1[CH3:33])=[O:18]>>[CH3:25][C@H:24]1[CH2:23][NH:22][CH2:21][C@@H:20]([CH3:33])[N:19]1[C:17]([O:5][CH2:4][C:3]1[C:2]([F:1])=[CH:9][C:8]([O:10][CH2:14][CH:13]=[CH2:12])=[CH:7][C:6]=1[F:11])=[O:18]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69141786HCID 69141786, compound

Procedure

2,6-Difluoro-4-(2-propenyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2,6-difluoro-4-hydroxybenzyl alcohol, allyl bromide and cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the methods described for Examples 54 and 96: NMR δH (400 MHz, DMSO-d6) 1.25 (6H, d, J 6.9 Hz), 2.75–2.87 (4H, m), 4.04 (2H, m), 4.51 (2H, dt, J 5.3, 1.5 Hz), 5.14 (2H, s), 5.32 (1H, dq, J 10.5, 1.5 Hz), 5.41 (1H, dq, J 17.3, 1.5 Hz), 6.00 (1H, ddt, J 17.3, 10.5, 5.3 Hz) and 6.45 (2H, m), NH not observed; HPLC (XTERRA, 50/80, 220 nm) 97.3% (3.89 min).

Workup

  1. customHPLC (XTERRA, 50/80, 220 nm) 97.3% (3.89 min)

Sources & evidence

ORD record
ord-0e04fecce26c4201b13701c621b06d63
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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