Water → (1RS,2RS)-1-(6-Benzyloxy-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol

HRID 278453노트

반응식

HRID 278453 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH:14]([CH2:20][N:21]1[CH2:26][CH2:25][C:24]([OH:35])([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[CH2:23][CH2:22]1)[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([OH:19])[CH:14]([CH2:20][N:21]1[CH2:22][CH2:23][C:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)([OH:35])[CH2:25][CH2:26]1)[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22628340(RS)-6-Benzyloxy-2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-ylmethyl]-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 22628392(1RS,2RS)-1-(6-Benzyloxy-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol수율 57.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

(RS)-6-Benzyloxy-2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-ylmethyl]-3,4-dihydro-2H-naphthalen-1-one (1.30 g, 2.77 mmol) in THF (15 ml) was added dropwise to a suspension of LiAlH4 (0.6 g, 15.5 mmol) in THF (20 ml) over 15 min (5-10° C.) and then stirred at RT for 2.5 hr. Distilled H2O (1 ml) and 4N NaOH (2 ml) followed by further H2O (2 ml), was added to quench the reaction and stirred vigorously 15 min., the mixture was then dried with Na2SO4, filtered and evaporated. The resulting crude liquid was chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH—NH4OH (100:5:0.25) to afford the title compound as a white foam (0.75 g, 1.6 mmol, 57%), MS m/e=472.4 (M+H+).

후처리

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. stirringstirred vigorously 15 min.
  5. dry with materialthe mixture was then dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting crude liquid was chromatographed over SiO2 (Merck 230-400 mesh)
  9. washeluting with CH2Cl2—MeOH—NH4OH (100:5:0.25)

출처 및 근거

ORD 기록
ord-076fd99e57d548c2b13c540975ab88a2
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359138B1

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