Water → HCID 22622886, compound

HRID 840380Notes

Reaction equation

HRID 840380 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([C:13](OC)=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.CC(C[AlH]CC(C)C)C.C(O)(C)C.O>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 14487Diisobutylaluminum hydrideHCID 10656590methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Product 1

HCID 22622886HCID 22622886, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

10.3 g (46.6 mmol) of (±)-2-methyl-3-oxo-6-(methoxycarbonyl)-3,4-dihydro-2H-1,4-benzoxazine is dissolved in 164 ml of tetrahydrofuran. After 330 ml of toluene is added, the solution is cooled to −15° C. At this temperature, 144.2 ml of a 20% DIBAH solution in toluene is added in drops within 30 minutes. A color change from yellow to orange takes place. After 45 minutes of stirring at −15° C., 31 ml of isopropanol is added in drops at this temperature, and 68 ml of water is added in drops at 0° C. After 2½ hours of vigorous stirring at room temperature, the precipitate that is produced is suctioned off, washed with tetrahydrofuran, and the filtrate is spun in. The residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol).

Workup

  1. additionis added in drops at 0° C
  2. stirringAfter 2½ hours of vigorous stirring at room temperature
  3. customthe precipitate that is produced
  4. washwashed with tetrahydrofuran
  5. customThe residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol)

Sources & evidence

ORD record
ord-9e5a0793d9b143029418ccd7890425c4
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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