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

HRID 1365341Notes

Reaction equation

HRID 1365341 reaction equation
[Cl-].[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]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 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 6228DimethylformamideSolvent2×

Procedure

To sodium chloride (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 added 4-methanesulfonyl-piperidine-carboxylic acid tert-butyl ester (500 mg) 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-6b2966ffed3c4d9f8ad00d3c24f47f78
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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