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

HRID 2102513Notes

Reaction equation

HRID 2102513 reaction equation
[Si](OCC(C)C[C@H:12]1[C:17](=[O:18])[NH:16][C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[O:13]1)(C(C)(C)C)(C)C.CCCC[N+](C[CH2:38][CH2:39][CH3:40])(CCCC)CCCC.[F-].C1C[O:45][CH2:44]C1>>[OH:45][CH2:44][C@@H:39]([CH3:38])[CH2:40][N:16]1[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[O:13][CH2:12][C:17]1=[O:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 69007075HCID 69007075, compound

Product 1

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

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-125cb531353c42b48b752547ae49134c
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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