Oxazole → HCID 68971731, compound

HRID 1726140Notes

Reaction equation

HRID 1726140 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.B.C1COCC1.[Li]C(C)(C)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH:30]=[O:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH:30]([OH:31])[C:2]2[O:1][CH:5]=[CH:4][N:3]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 9255OxazoleHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 2723981Borane;tetrahydrofuranHCID 178418306HCID 178418306, compound

Product 1

HCID 68971731HCID 68971731, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of oxazole (420 mg, 6.08 mmol) in THF (15 mL) was added BH3-THF (1.0M in THF, 6.69 mL, 6.69 mmol). The mixture was stirred at room temperature for 1 hour. After cooling to −78° C., t-BuLi (1.7M, 4.29 mL, 7.30 mmol) was introduced to the mixture and stirred at this temperature for 30 min. 4-Formyl-piperidine-1-carboxylic acid tert-butyl ester (1.30 g, 6.08 mmol) was added dropwise and the mixture was stirred at −78° C. for 3 hours. Work-up and purification gave 4-(hydroxy-oxazol-2-yl-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a white foam (1.227 g, 71%).

Workup

  1. temperatureAfter cooling to −78° C.
  2. stirringstirred at this temperature for 30 min
  3. stirringthe mixture was stirred at −78° C. for 3 hours
  4. customWork-up and purification

Sources & evidence

ORD record
ord-835ecd3af05a409a89e17b45104d0923
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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