tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate → Tert-butyl 4-(6-{2-[3-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate

HRID 1465483Notes

Reaction equation

HRID 1465483 reaction equation
[Cl-].[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][CH:29]=1)[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([C:32]1[N:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]2)=[CH:34][CH:33]=1)=O>>[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:30][C:32]2[N:37]=[CH:36][C:35]([N:38]3[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]3)=[CH:34][CH:33]=2)[CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 58181229tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylateHCID 86651844[3-(Hydroxymethyl)benzyl](triphenyl)phosphonium chloride

Product 1

HCID 67267046Tert-butyl 4-(6-{2-[3-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylateYield 70.3%

Procedure

By a method similar to Production Example 108, step 4, [3-(hydroxymethyl)benzyl](triphenyl)phosphonium chloride (1.675 g, 3.998 mmol) and tert-butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate (1.165 g, 4.000 mmol) were condensed to give tert-butyl 4-(6-{2-[3-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate (1.111 g, yield 70.2%, E/Z mixture) as a yellow solid.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-c52007072218454c832e66cf7054a59a
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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