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

HRID 1819281Notes

Reaction equation

HRID 1819281 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 L-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-21d755ba686a415a856d5176509ef75b
Source dataset
uspto-grants-2009_10
Patent number
US07601745B2

Reaction notes

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