Tetrahydrofuran → (S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-6-methoxy-4H-benzo[1,4]oxazin-3-one

HRID 2103194Notes

Reaction equation

HRID 2103194 reaction equation
[Si:1]([O:8][CH2:9][CH: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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C[O:46][CH2:45]C1>>[Si:1]([O:8][CH2:9][C@@H:10]([CH3:23])[CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([O:46][CH3:45])[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:22])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 689101304-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68912948(S)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-6-methoxy-4H-benzo[1,4]oxazin-3-one

Procedure

To a 100 mL flask was charged 4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (1.0 equiv) and Tetrabutylammonium flouride monohydrate (1.3 equiv) and dissolved in 40 mL dry THF. The reaction was stirred in rt under an inert atmosphere for 20-24 hours. The reaction mixture was concentrated and purified by CC (Heptane/EtOAc).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by CC (Heptane/EtOAc)

Sources & evidence

ORD record
ord-39492f8e6e9f453d9db640aa11ec0777
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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