Tetrabutylammonium Fluoride → (S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1191511Notes

Reaction equation

HRID 1191511 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([CH3:23])[CH2:11][N:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:22])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C@@H:10]([CH3:23])[CH2:11][N:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:22]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68910909(S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68915929(S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-oneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction flask was charged with (S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (3.92 g, 11.7 mmol), and TBAF (4.78 g, 15.2 mmol) in THF (30 mL) and stirred at rt for 20 h. The reaction mixture was concentrated, dissolved in EtOAc, and washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 3:7) to give the title compound (2.52 g, 98%). 1H NMR (CDCl3) δ 7.05-6.95 (m, 4H), 4.63 (s, CH2), 4.23 (dd, J=10.3 Hz, J=13.9 Hz, 1H), 3.56 (dd, J=4.8 Hz, J=13.9 Hz, 1H), 3.52-3.49 (m, 1H), 3.46-3.38 (m, 1H), 2.92-2.85 (m, 1H), 2.09-1.97 (m, 1H), 1.06 (d, J=7.3 Hz, CH3).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 3:7)

Sources & evidence

ORD record
ord-38e6d62a5aa349ae843f19412329ba5f
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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