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 63961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63961
Cl.[CH2:2]([O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:18]([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:17]([CH3:26])[N:16]=[C:15]2[S:27][C:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[C:14]=12)[CH:3]=[CH2:4].[BH4-].[Na+]>C(O)C>[CH2:2]([O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:18]([CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:17]([CH3:26])[N:16]=[C:15]2[S:27][C:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[C:14]=12)[CH:3]=[CH2:4]

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 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(oxo)acetate hydrochloride salt (Step 6, 1.1 g, 2.56 mmol) in ethanol (20 mL) was added sodium borohydride (145 mg, 3.84 mmol), 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 organic layer was separated, washed with brine (10 mL), dried over MgSO4, filtered and concentrated in vacuo to give a mixture of diastereoisomers of the title compound as a pale orange gum, 1.1 g, in a 91% yield. LCMS (2 min acidic) 1.53 min 52-81% pure by UV, ES+/AP+ 452. 1HNMR (400 MHz, CDCl3 δ ppm 1.17-1.21 (m, 3H), 1.53-1.64 (m, 2H), 1.71-1.87 (m, 4H), 2.43 (s, 3H), 2.63 (s, 3H), 2.81 (t, 2H), 4.08-4.22 (m, 2H), 4.47-4.51 (m, 2H), 5.08-5.17 (m, 2H), 5.18 (s, 1H), 5.86 (m, 1H), 6.79 (s, 1H), 6.81-6.85 (m, 1H), 7.02 (d, 1H).

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 organic layer was separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give

Quellen und Nachweise

ORD-Eintrag
ord-f0254e30797e46ccb6cb8fed233011a8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447116B2

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