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

HRID 278419ノート

反応式

HRID 278419 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-fc919ed63df14ce78d3b42877bdafac4
出典データセット
uspto-grants-2002_03
特許番号
US06359138B1

反応ノート

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