Cesium carbonate → (R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 2102510Notes

Reaction equation

HRID 2102510 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.Br[CH2:13][C@@H:14]([CH3:17])[CH2:15][OH:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[OH:16][CH2:15][C@H:14]([CH3:17])[CH2:13][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][C:3]1=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 10986449(S)-(+)-3-Bromo-2-methyl-1-propanol

Product 1

HCID 68910321(R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-oneYield 147.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A 25 mL flask was charged with 4H-benzo[1,4]oxazin-3-one (0.100 g, 0.670 mmol), (S)-3-bromo-2-methylpropanol (0.103 g, 0.670 mmol) and cesium carbonate (0.208 g, 0.670 mmol) in MeCN (10 mL) and stirred at 40° C. for 2 days. The reaction mixture was quenched with water (5 mL), and the product extracted into EtOAc (2×10 mL). The combined organic layers were dried (Na2SO4) and evaporated to give the crude title compound (108LM40-37) (0.219 g).

Workup

  1. customThe reaction mixture was quenched with water (5 mL)
  2. extractionthe product extracted into EtOAc (2×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-10cbc9ad134248429771a9f8ed777792
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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