1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → (S)-4-(3-Hydroxy-2-methylpropyl)-6-methoxy-4H-benzo[1,4]oxazin-3-one

HRID 2103197Notes

Reaction equation

HRID 2103197 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([CH3:25])[CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:24])(C(C)(C)C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCCCCCC.CCOC(C)=O>[OH:8][CH2:9][C@@H:10]([CH3:25])[CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:24]

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68912948(S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-6-methoxy-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68911239(S)-4-(3-Hydroxy-2-methylpropyl)-6-methoxy-4H-benzo[1,4]oxazin-3-oneYield 100%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The compound (S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-6-methoxy-4H-benzo[1,4]oxazin-3-one (111MF32) (4.03 g, 12.0 mmol) and tetrabutylammonium flouride monohydrate (4.46 g, 16.0 mmol) were mixed according to GP8. CC (SiO2; Heptane/EtOAc 4:1-4) gave the title compound (111MF34) (2.70 g, 100%). 1H NMR (CDCl3) δ 6.91 (d, J=8.8 Hz, 1H), 6.63 (d, J=2.8 Hz, 1H), 6.54 (dd, J=2.8 Hz, J=8.8 Hz, 1H), 4.57 (s, 2H), 4.19 (dd, J=9.4 Hz, J=14.6 Hz, 1H), 3.78 (s, 3H), 3.56-3.39 (m, 3H), 2.84 (s, 1H), 2.09-1.99 (m, 1H), 1.05 (d, J=7.2 Hz, 3H); 13C NMR (CDCl3) 165.8, 155.5, 139.5, 129.4, 117.4, 107.7, 103.0, 67.7, 63.8, 56.0, 43.6, 34.1, 15.0.

Sources & evidence

ORD record
ord-f93f9e457c2142f992ed7430319c898a
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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