Tetrabutylammonium Fluoride → 4-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol

HRID 273037

반응식

HRID 273037 반응식
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][CH2:21][C:15]1([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 68577980N-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methyl}pyridin-2-amine

생성물 1

HCID 685779444-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methyl}pyridin-2-amine (2.099 g, 5.27 mmol) and tetrabutylammonium fluoride (1M solution in THF, 5.80 ml, 5.80 mmol) were stirred in THF (20 ml) at room temperature for 24 hours until complete. THF was removed in vacuo and the residue partitioned between dichloromethane (75 ml) and sodium bicarbonate (50 ml). The organic layer was washed further with sodium bicarbonate (2×50 ml), then separated and dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on Biotage® silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 90:10:1 by volume) to give the title compound (862 mg, 58%) as a solid. LRMS APCI+ m/z 285 [MH]+.

후처리

  1. customTHF was removed in vacuo
  2. customthe residue partitioned between dichloromethane (75 ml) and sodium bicarbonate (50 ml)
  3. washThe organic layer was washed further with sodium bicarbonate (2×50 ml)
  4. customseparated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography on Biotage® silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 90:10:1 by volume)

출처 및 근거

ORD 기록
ord-f99e569dffcb4be198e9e045727d6d8f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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