Water → HCID 67781703, compound

HRID 1756255Notes

Reaction equation

HRID 1756255 reaction equation
B#B.[F:3][C:4]([F:19])([F:18])[C:5]1[CH:6]=[CH:7][C:8]2[O:15][C:12]3([CH2:14][CH2:13]3)[C:11](=O)[NH:10][C:9]=2[CH:17]=1.O>O1CCCC1>[F:19][C:4]([F:3])([F:18])[C:5]1[CH:6]=[CH:7][C:8]2[O:15][C:12]3([CH2:13][CH2:14]3)[CH2:11][NH:10][C:9]=2[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328200DiboronHCID 67781429HCID 67781429, compound

Product 1

HCID 67781703HCID 67781703, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice cooling, 1.1 ml of a 1M solution of diborane in tetrahydrofuran were added dropwise to a solution of 1.07 g of 3,4-dihydro-6-trifluoromethyl-3-oxo-2H-1,4-benzoxazine-2-spiro-cyclopropane in tetrahydrofuran, followed by stirring at room temperature for 4 hours. The reaction mixture was ice cooled, to which iced water was added, followed by stirring at room temperature for 15 minutes. The reaction mixture was extracted with ethyl ether and the extract was dried over magnesium sulfate. The ethyl ether was distilled off and the residue was purified by chromatography on a silica gel column, whereby 0.96 g of the title compound was obtained (yield: 95%).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 15 minutes
  3. extractionThe reaction mixture was extracted with ethyl ether
  4. dry with materialthe extract was dried over magnesium sulfate
  5. distillationThe ethyl ether was distilled off
  6. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cbc677962f0a4976bc17982befba6b2a
Source dataset
uspto-grants-1995_08
Patent number
US05440036

Reaction notes

Loading…