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 63947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63947
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]

Komponenten

4

Edukt 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

Produkt 1

HCID 69672380Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(hydroxy)acetateAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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, 1N, 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, 1 H) 6.81-6.85 (m, 1 H) 6.79 (s, 1 H) 5.86 (m, 1 H) 5.18 (s, 1 H) 5.08-5.17 (m, 2 H) 4.47-4.51 (m, 2 H) 4.08-4.22 (m, 2 H) 2.81 (t, J=6.2 Hz, 2 H) 2.63 (s, 3 H) 2.43 (s, 3 H) 1.71-1.87 (m, 4 H) 1.53-1.64 (m, 2 H) 1.17-1.21 (m, 3 H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ba30a747fa7149e6b65ad6b443842d55
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447116B2

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