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

HRID 278419노트

반응식

HRID 278419 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][N:14]1[CH2:19][CH2:18][C:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)([OH:20])[CH2:16][CH2:15]1)[CH2:7][CH2:6]2.B(Br)(Br)Br.C(Cl)Cl.CO.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][N:14]1[CH2:19][CH2:18][C:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)([OH:20])[CH2:16][CH2:15]1)[CH2:7][CH2:6]2

참가 물질

7

반응물 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 22628368(RS)-1-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol

생성물 1

HCID 9842071(RS)-1-(6-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol수율 616.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To (RS)-1-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (843 mg, 2.22 mmol) in CH2Cl2 (20 ml) was added 1M BBr3/CH2Cl2 (4.88 ml, 4.88 mmol, 2.2 eq.) over 15 min at −78° C., the mixture was then allowed to warm to RT over 40 min. MeOH (3 ml), H2O (20 ml) and NaHCO3 (20 ml) were added and the mixture extracted with CH2Cl2 (4×50 ml). The extracts were washed with satd. NaCl solution (30 ml), dried (Na2SO4), filtered and evaporated, to afford the crude product as a yellow foam. Chromatography over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (97:3) afforded (RS)-1-(6-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol as a white foam (500 mg, 13.68 mmol, 61%), MS m/e=366.2 (M+H+).

후처리

  1. extractionthe mixture extracted with CH2Cl2 (4×50 ml)
  2. washThe extracts were washed with satd
  3. dry with materialNaCl solution (30 ml), dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto afford the crude product as a yellow foam
  7. washChromatography over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (97:3)

출처 및 근거

ORD 기록
ord-fc919ed63df14ce78d3b42877bdafac4
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359138B1

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