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

HRID 2103171Notes

Reaction equation

HRID 2103171 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

The compound (S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (108LM24-21) (3.92 g, 11.7 mmol) and TBAF (4.78 g, 15.2 mmol) in THF (30 mL) were reacted according to GP3 to give the title compound (108LM26-23) (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).

Sources & evidence

ORD record
ord-fd989c20c6494d66a2d6962b29ae3363
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

Loading…