2,6-Difluorobenzyl alcohol → 2,6-Difluorobenzyl 4-tert-butoxycarbonyl-cis-2,6-dimethylpiperazine-1-carboxylate

HRID 1794092Notes

Reaction equation

HRID 1794092 reaction equation
Cl[C:2]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][C@@H:5]1[CH3:18])=[O:3].[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:21]=1[CH2:22][OH:23]>>[C:14]([O:13][C:11]([N:7]1[CH2:8][C@@H:9]([CH3:10])[N:4]([C:2]([O:23][CH2:22][C:21]2[C:20]([F:19])=[CH:27][CH:26]=[CH:25][C:24]=2[F:28])=[O:3])[C@@H:5]([CH3:18])[CH2:6]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 879212,6-Difluorobenzyl alcoholHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 691414042,6-Difluorobenzyl 4-tert-butoxycarbonyl-cis-2,6-dimethylpiperazine-1-carboxylate

Procedure

2,6-Difluorobenzyl 4-tert-butoxycarbonyl-cis-2,6-dimethylpiperazine-1-carboxylate was prepared from cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine and 2,6-difluorobenzyl alcohol according to the method described for Example 54 to give the product as a colourless gum (0.251 g, 65%); Rf (Silica, isopropyl ether) 0.35; δH (400 MHz, CDCl3) 7.29 (1H, m), 6.90 (2H, m), 5.23 (2H, s), 4.16 (2H, m), 3.92 (2H, br), 2.95 (2H, br), 1.47 (9H, s), 1.21 (6H, d, J 6.8 Hz).

Sources & evidence

ORD record
ord-2aa98fdb3913405eb0b6a50cfcdd272b
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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