Potassium tert-butoxide → HCID 90236046, compound

HRID 81115Notes

Reaction equation

HRID 81115 reaction equation
[CH2:1]([N:8]([C:23](=[O:26])[CH2:24]I)[C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]1[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>C1COCC1>[CH2:1]([N:8]1[C:23](=[O:26])[CH2:24][O:22][CH:10]2[CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14][CH:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 131731894HCID 131731894, compound

Product 1

HCID 90236046HCID 90236046, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-tert-butyl 4-[benzyl(iodoacetyl)amino]-3-hydroxypiperidine-1-carboxylate (172 g, 363 mmol) in THF (1500 mL) was added t-BuOK (48.72 g, 435 mmol) in portions at 0° C. The mixture was stirred at room temperature for 2 h. The mixture was poured into ice-water (400 mL) and extracted with EtOAc (200 mL×2). The organic layer was washed with brine (200 mL), dried over sodium sulfate, and concentrated under reduced pressure to give tert-butyl 1-benzyl-2-oxooctahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate as a mixture of trans diastereomers, which was used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc (200 mL×2)
  2. washThe organic layer was washed with brine (200 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bde9d5bb04434cc9b6b2eba81a8f64f4
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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