Water → 6-(4-Morpholinyl)-2-pyridinemethanol

HRID 2183507노트

반응식

HRID 2183507 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[N:33]=[C:32]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:31]=[CH:30][CH:29]=1)(C(C)(C)C)(C)C.O>C1COCC1>[N:34]1([C:32]2[N:33]=[C:28]([CH2:27][OH:26])[CH:29]=[CH:30][CH:31]=2)[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 224731974-[6-(Tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine

생성물 1

HCID 224732166-(4-Morpholinyl)-2-pyridinemethanol수율 82.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of tetrabutylammonium fluoride (1.44 mmol) in THF (1.0 M, 1.44 ml) was added to a stirred solution of 4-[6-(tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine (370 mg, 1.2 mmol) in THF (10 ml) at room temperature under N2 and the reaction mixture was stirred at room temperature for 1 h. H2O (30 ml) was added and the organic were extracted with EtOAc (150 ml), then washed with brine (50 ml), dried and concentrated under reduced. The mixture was purified by column chromatography on silica using 100% Et2O as eluent to yield the desired hydroxymethylpyridine (192 mg, 82%). 1H NMR (360 MHz, CDCl3) δ 7.49 (1H, dd, J=8.4, 7.4 Hz), 6.57 (1H, d, J=7.4 Hz), 6.51 (1H, d, J=8.4 Hz), 4.62 (2H, s), 3.83 (4H, t, J=4.9 Hz), 3.50 (4H, t, J=4.9 Hz).

후처리

  1. extractionthe organic were extracted with EtOAc (150 ml)
  2. washwashed with brine (50 ml)
  3. customdried
  4. concentrationconcentrated
  5. customThe mixture was purified by column chromatography on silica using 100% Et2O as eluent

출처 및 근거

ORD 기록
ord-7dbea7aeb97049f29426dc30322ce781
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900209B2

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