Sodium borohydride → Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(hydroxy)acetate

HRID 2406383ノート

反応式

HRID 2406383 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:33])[C:6]([C:8]1[C:9]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[O:29][CH2:30][CH:31]=[CH2:32])=[C:10]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[S:15][C:11]2=[N:12][C:13]=1[CH3:14])=[O:7])[CH3:3].[BH4-].[Na+]>C(O)C>[CH2:2]([O:4][C:5](=[O:33])[CH:6]([C:8]1[C:9]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[O:29][CH2:30][CH:31]=[CH2:32])=[C:10]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[S:15][C:11]2=[N:12][C:13]=1[CH3:14])[OH:7])[CH3:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 69672800Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(oxo)acetate hydrochloride salt

生成物 1

HCID 69672380Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(hydroxy)acetate収率 95.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of [4-(2-Allyloxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-oxo-acetic acid ethyl ester hydrochloride (1.1 g, 2.56 mmols) in ethanol (20 mL) was added sodium borohydride (145 mg, 1.5 eq, 3.84 mmols), and the reaction was stirred at room temperature for 5 minutes. The reaction was concentrated in vacuo, and the residue was partitioned between ethyl acetate (20 mL) and hydrochloric acid (aqueous, 1 N, 30 mL). The organics were separated, washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to give crude [4-(2-allyloxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-hydroxy-acetic acid ethyl ester as a pale orange gum 1.1 g (91% yield). LCMS (2 min acidic) 1.53 min 52-81% pure by UV, ES+/AP+ 452. HNMR (CDCl3)>80% pure 7.02 (d, J=7.4 Hz, 1H) 6.81-6.85 (m, 1H) 6.79 (s, 1H) 5.86 (m, 1H) 5.18 (s, 1H) 5.08-5.17 (m, 2H) 4.47-4.51 (m, 2H) 4.08-4.22 (m, 2H) 2.81 (t, J=6.2 Hz, 2H) 2.63 (s, 3H) 2.43 (s, 3H) 1.71-1.87 (m, 4H) 1.53-1.64 (m, 2H) 1.17-1.21 (m, 3H).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate (20 mL) and hydrochloric acid (aqueous, 1 N, 30 mL)
  3. customThe organics were separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f3624e3b2c584b12988a1494d511db74
出典データセット
uspto-grants-2014_08
特許番号
US08809363B2

反応ノート

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