Proton sponge → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627117노트

반응식

HRID 627117 반응식
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][OH:17])[C:13](=[O:18])[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:26]N(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][O:17][CH3:26])[C:13](=[O:18])[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 89852514(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(hydroxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 89852461(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(hydroxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (17.37 g, 46.75 mmol) in DCM (480 mL) was added N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine (60.1 g, 280.51 mmol). Then it was cooled to 0° C. and trimethyloxonium tetrafluoroborate (20.74 g, 140.25 mmol) was added. It was then stirred at rt for 6 h. Then it was concentrated under reduced pressure. The residue was then taken up in 100 mL Et2O and filtered, washed with 400 mL Et2O. The organic layer was then washed with 10% citric acid, aq. NaHCO3, brine, dried over MgSO4, filtered and concentrated to afford the desired product (16.73 g, 93%) as an oil.

후처리

  1. concentrationThen it was concentrated under reduced pressure
  2. filtrationfiltered
  3. washwashed with 400 mL Et2O
  4. washThe organic layer was then washed with 10% citric acid, aq. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-884217cda59a4cf8a729859e1e11343d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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