Triethylamine → 1-Boc-4-(4-Ethoxycarbonyl-4,5-dihydrothiazol-2-yl)piperidine

HRID 1158842Notes

Reaction equation

HRID 1158842 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:17]([O:19][C:20](=[O:25])[C@H:21]([CH2:23][SH:24])[NH2:22])[CH3:18].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:24][CH2:23][CH:21]([C:20]([O:19][CH2:17][CH3:18])=[O:25])[N:22]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 2723617Ethyl cysteinate hydrochloride

Product 1

HCID 666795511-Boc-4-(4-Ethoxycarbonyl-4,5-dihydrothiazol-2-yl)piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-formyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 eq, 13 mmol) was dissolved under inert conditions in 40 ml toluene. To this solution cystein ethylester hydrochloride (1.6 eq, 21 mmol) and triethylamine (1.6 eq, 21 mmol) were added. The mixture was refluxed for 14 h. The generated water was removed with a Dean & Stark trap.

Workup

  1. temperatureThe mixture was refluxed for 14 h
  2. customThe generated water was removed with a Dean & Stark trap

Sources & evidence

ORD record
ord-2abc9dfbe35443fe87c803c3a488930b
Source dataset
uspto-grants-2010_10
Patent number
US07812041B2

Reaction notes

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