Triethylamine → HCID 20810193, compound

HRID 895112Notes

Reaction equation

HRID 895112 reaction equation
[ClH:1].[CH3:2][C@@H:3]1[C:8](=O)[NH:7][C:6]2[CH:10]=[C:11]([CH2:14][NH2:15])[CH:12]=[CH:13][C:5]=2[O:4]1.[F:16][C:17]([F:23])([F:22])[CH2:18][CH2:19][CH:20]=O.C([N:26](CC)CC)C.[BH4-].[Na+]>C(OCC)(=O)C.O.O1CCCC1.CO>[ClH:1].[ClH:1].[CH3:2][C@@H:3]1[C:8]([NH2:26])=[N:7][C:6]2[CH:10]=[C:11]([CH2:14][NH:15][CH2:20][CH2:19][CH2:18][C:17]([F:23])([F:22])[F:16])[CH:12]=[CH:13][C:5]=2[O:4]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 27770834,4,4-TrifluorobutanalHCID 4311764Sodium borohydrideHCID 20810229HCID 20810229, compound

Product 1

HCID 20810193HCID 20810193, compoundYield 88.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

780 mg (3.668 mmol) of (2R)-methyl-3-oxo-6-aminomethyl-2H-1,4-benzoxazine-hydrochloride, 462.4 mg (3.668 mmol) of 4,4,4-trifluorobutyraldehyde and 371.2 mg (3.668 mmol) of triethylamine are dissolved in a mixture that consists of methanol and tetrahydrofuran (4:1). After three hours of stirring at room temperature, 75.2 mg of sodium borohydride is added. After stirring overnight at room temperature, the batch is added to water and shaken three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried and spun in. After chromatography on silica gel (mobile solvent: dichloromethane/isopropanol, 608.8 mg (55%) of the desired compound is obtained.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. customdried

Sources & evidence

ORD record
ord-fb29af4db05b4657be3c10f3998387f5
Source dataset
uspto-grants-2005_07
Patent number
US06914059B2

Reaction notes

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