Methyl 2-(piperidin-1-yl)pyridine-4-carboxylate → [2-(Piperidin-1-yl)pyridin-4-yl]methanol

HRID 1174510노트

반응식

HRID 1174510 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][N:22]=2)[C:16](OC)=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1>[N:7]1([C:13]2[CH:14]=[C:15]([CH2:16][OH:17])[CH:20]=[CH:21][N:22]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

참가 물질

4

반응물 2

HCID 18525843Methyl 2-(piperidin-1-yl)pyridine-4-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 18525842[2-(Piperidin-1-yl)pyridin-4-yl]methanol수율 65.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of LAH (5.5 g, 0.145 mol) in dry THF (500 mL) at 0° C. was added methyl 2-piperidin-1-ylisonicotinate (18 g, 0.095 mol) in dry THF (100 mL) under N2 atmosphere. The reaction mixture was stirred at RT for 4 h and quenched with 10% aqueous NaOH solution at −20° C. The solid was filtered off, washed with THF and concentrated. The residue was dissolved in CH2Cl2 (250 mL), washed with water, brine and dried. The solvent was removed under vacuum and the crude was purified by column chromatography over silica gel (CHCl3/MeOH, 9:1) to give (2-piperidin-1-yl pyridin-4-yl)methanol (12 g, 65%). 1H NMR (DMSO-d6) δ 7.98 (d, J=5.2 Hz, 1H), 6.71 (s, 1H), 6.51 (br d, 1H), 5.24 (t, J=5.2 Hz, 1H), 4.41 (d, J=5.2 Hz, 2H), 3.49-3.46 (m, 4H), 1.58-1.50 (m, 6H).

후처리

  1. customquenched with 10% aqueous NaOH solution at −20° C
  2. filtrationThe solid was filtered off
  3. washwashed with THF
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2 (250 mL)
  6. washwashed with water, brine
  7. customdried
  8. customThe solvent was removed under vacuum
  9. customthe crude was purified by column chromatography over silica gel (CHCl3/MeOH, 9:1)

출처 및 근거

ORD 기록
ord-ef43a2b0866d40839e76d95162fe3c53
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838522B2

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