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Sodium hydride → 4-(Thiazol-2-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 881555
Notes
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Reaction equation

HRID 881555 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][N:5]=[C:4]1[SH:8].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19](S(C)(=O)=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([S:8][C:4]2[S:3][CH:7]=[CH:6][N:5]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22504298Tert-butyl 4-(methylsulfonyl)piperidine-1-carboxylateHCID 178527881HCID 178527881, compound

Product 1

HCID 185389074-(Thiazol-2-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterYield 30.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent
2×

Procedure

To sodium hydride (60% wt. suspension in mineral oil, 108 mg) in dry DMF (5 ml) was added 1,3-thiazole-2-thiol (315 mg) at 0° C. After 30 minutes, 4-methanesulfonyl-piperidine-carboxylic acid tert-butyl ester (500 mg) was added as a solution in DMF (2 ml) and the reaction mixture was warmed up to room temperature overnight, then heated at 50° C. for 3 hours. Aqueous work-up and purification on silica yielded 4-(thiazol-2-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (174 mg).

Workup

  1. temperatureheated at 50° C. for 3 hours
  2. customAqueous work-up and purification on silica

Sources & evidence

ORD record
ord-471c885b0f6f4b7982f14c972acf92d3
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993563B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes