Sodium hydride → cis-2,6-Dimethyl-piperazine-1-carboxylic acid 6-(3-methyl-butoxy)-pyridin-3-ylmethyl ester

HRID 1794088Notes

Reaction equation

HRID 1794088 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1.[H-].[Na+].C(OC([N:24]1[CH2:29][C@@H:28]([CH3:30])[N:27]([C:31](Cl)=[O:32])[C@@H:26]([CH3:34])[CH2:25]1)=O)(C)(C)C>>[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][O:13][C:31]([N:27]2[C@H:28]([CH3:30])[CH2:29][NH:24][CH2:25][C@@H:26]2[CH3:34])=[O:32])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 22219862[6-(3-Methyl-butoxy)-pyridin-3-yl]-methanolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69142432cis-2,6-Dimethyl-piperazine-1-carboxylic acid 6-(3-methyl-butoxy)-pyridin-3-ylmethyl ester

Procedure

cis-2,6-Dimethyl-piperazine-1-carboxylic acid 6-(3-methyl-butoxy)-pyridin-3-ylmethyl ester was prepared from [6-(3-Methyl-butoxy)-pyridin-3-yl]-methanol (0.19 g), sodium hydride (60%, 0.048 g) and 4-tert-butoxycarbonyl-1-chlorocarbonyl-cis-2,6-dimethylpiperazine (0.25 g) according to the method described in Example 54 to give the product as a pale oil (0.052 g, 13%): δH (400 MHz, CDCl3) 8.15 (1H, d, J 2.5 Hz), 7.58 (1H, dd, J 8.5, 2.5 Hz), 6.71 (1H, d, J 8.5 Hz), 5.07 (2H, s), 4.32 (2H, t, J 7 Hz), 4.18 (2H, m), 3.95 (2H, m), 2.95 (2H, m), 1.81 (1H, nonet, J 7 Hz), 1.67 (2H, q, J 7 Hz), 1.47 (9H, s), 1.22 (6H, d, J 7 Hz) and 0.96 (6H, d, J 6.5 Hz); HPLC (XTERRA, 50/80, 235 nm) 91% (7.19 min).

Sources & evidence

ORD record
ord-00225f9a690e48f5b15e5ae2ca4768dc
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…