Thiazole → HCID 71183822, compound

HRID 2274154Notes

Reaction equation

HRID 2274154 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:6]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)=[O:7]>O1CCCC1.CCCCCC>[OH:7][CH:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1

Participants

5

Reactant 2

HCID 9256ThiazoleHCID 99644481-Boc-piperidine-3-carboxaldehyde

Product 1

HCID 71183822HCID 71183822, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, 1.25 ml (17.62 mmol) of thiazole were dissolved in 20 ml of tetrahydrofuran at −70° C. 11.1 ml (17.62 mmol) [15% in n-hexane] were subsequently added dropwise at such a rate that the temperature did not exceed −67° C. The mixture was warmed to room temperature, then cooled to −70° C., and 3.76 g (17.62 mmol) of tert-butyl 3-formylpiperidine-1-carboxylate, dissolved in 5 ml of tetrahydrofuran, were added dropwise. The mixture was stirred at −70° C. for 1 h, warmed to room temperature and stirred for a further 2 h. Conventional work-up gave 5.18 g of tert-butyl 3-(hydroxythiazol-2-ylmethyl)-piperidine-1-carboxylate; HPLC/MS (M+H)+=299 as oil.

Workup

  1. customdid not exceed −67° C
  2. temperaturecooled to −70° C.
  3. additionwere added dropwise
  4. temperaturewarmed to room temperature
  5. stirringstirred for a further 2 h

Sources & evidence

ORD record
ord-87a2e5f0bde9449b9d92fe09f07c8f84
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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