Methanol → HCID 90236513, compound

HRID 1852723Notes

Reaction equation

HRID 1852723 reaction equation
[CH2:1]([N:8]1[C:13](=O)[CH2:12][O:11][C@@H:10]2[CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][C@@H:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]2[CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][CH:9]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 90236047trans-tert-butyl 1-benzyl-2-oxooctahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate

Product 1

HCID 90236513HCID 90236513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-tert-butyl 1-benzyl-2-oxooctahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate (126 g, 346 mmol) in anhydrous THF (2 L) was added borane methylsulfide complex (109 mL, 1.038 mol) drop wise at 0° C. The mixture was stirred at room temperature overnight. Methanol (300 mL) was added to the mixture at room temperature and heated to reflux for 1 h. The mixture was washed with saturated NaHCO3 and brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford tert-butyl 1-benzyloctahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate as a mixture of trans diastereomers.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. washThe mixture was washed with saturated NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dd105c47cb1f4e888995beb582b74196
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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