2-(Tributylstannyl)pyridine → HCID 10863584, compound

HRID 2270413Notes

Reaction equation

HRID 2270413 reaction equation
C([Sn](CCCC)(CCCC)C1C=CC=CN=1)CCC.[CH2:20]([O:22][C:23]([C:25]1([S:44]([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21]>[OH-].[Na+]>[CH2:20]([O:22][C:23]([C:25]1([S:44]([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:36][CH:37]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21].[CH3:54][O:53][C:50]1[CH:49]=[CH:48][C:47]([S:44]([C:25]2([C:23]([OH:24])=[O:22])[CH2:30][CH2:29][N:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=4)=[CH:34][CH:33]=3)[CH2:27][CH2:26]2)(=[O:46])=[O:45])=[CH:52][CH:51]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 10885529HCID 10885529, compound

Product 2

HCID 10863584HCID 10863584, compoundHCID 10885529HCID 10885529, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-(4-Methoxy-benzenesulfonyl)-1-(4-pyridin-2-yl-benzyl)-piperidine-4-carboxylic acid ethyl ester was prepared according to the general method outlined in example 261. Starting from 1-(4-Bromo-benzyl)-4-4-(4-methoxy-benzensulfonyl)-piperidine-4-carboxylic acid ethyl ester (4.65 g, 9.38 mmol) and 2-(tributylstannyl)-pyridine (12.08 g, 32.8 mmol). Yield 2.79 g (60%); brown oil; MS: 495.1 (M+H)+4-(4-Methoxy-benzenesulfonyl)-1-(4-pyridin-2-yl-benzyl)-piperidine-4-carboxylic acid was prepared starting from 4-(4-methoxy-benzenesulfonyl)-1-(4-pyridin-2-yl-benzyl)-piperidine-4-carboxylic acid ethyl ester (1.83 g, 3.7 mmol) dissolved in TBF:methanol (3:1 150 ml) and 10 N NaOH (10 ml). The resulting reaction mixture was worked up as outlined in example 83. Yield 1.38 g (80%); off white solid; mp 217° C.; MS: 466.9 (M+H)+

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-5eb399456b16413ea4c2c765082c0f2b
Source dataset
uspto-grants-2001_12
Patent number
US06331563B1

Reaction notes

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