3-(Chloromethyl)pyridine → 1-tert-Butoxycarbonyl-2(S)-(2-(3-pyridylmethoxy)ethyl)-4-(1-naphthoyl)piperazine

HRID 1598461Notes

Reaction equation

HRID 1598461 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][OH:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 129668321-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine

Product 1

HCID 228841261-tert-Butoxycarbonyl-2(S)-(2-(3-pyridylmethoxy)ethyl)-4-(1-naphthoyl)piperazine

Procedure

1-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-(1-naphthoyl)piperazine (0.300 g, 0.780 mmol) was reacted with sodium hydride (0.312 g, 60% dispersion in oil, 7.8 mmol) and 3-chloromethylpyridine (0.497 g, 3.9 mmol) according to the procedure described in Example 7, Step C. The crude product was chromatographed on silica gel with 3% methanol in chloroform. The title compound was obtained as an oil, (0.180 g).

Workup

  1. customThe crude product was chromatographed on silica gel with 3% methanol in chloroform

Sources & evidence

ORD record
ord-eaca8228c74d4c6aac6992b408809500
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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