Реакция #64644

Уравнение реакции

2,3-Dihydro-2-oxo-1-phenyl-3-(4-pyridinylmethyl)-1H-indole-3-butanoic acid ethyl ester hydrochloride

borane

MeOH

→

1,3-Dihydro-3-(4-hydroxybutyl)-1-phenyl-3-(4-pyridinylmethyl)-2H-indol-2-one Hydrochloride

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Концентрированиеthe mixture was concentrated in vacuo
2. 2
   workup.WAITThe residue was digested with 100 ml 1N HCl for 3 hours at 80° C.
3. 3
   Концентрированиеthe solution was concentrated
4. 4
   ДругоеThe residue was partitioned between 200 ml EtOAc and 100 ml 5% NaHCO3
5. 5
   ПромывкаThe organic phase was washed with water and brine
6. 6
   Сушкаdried over MgSO4
7. 7
   Фильтрацияfiltered
8. 8
   workup.ADDITIONtreated with 44 ml 1N HCl-Et2O
9. 9
   Другоеevaporated in vacuo
10. 10
    workup.WAITleft
11. 11
    workup.WAITstanding overnight
12. 12
    ФильтрацияThe resulting crystals were collected by filtration
13. 13
    Промывкаwashed with Et2O
14. 14
    Другоеdried
15. 15
    Другоеto give the product in 30% (2.72 g)
16. 16
    Другоеyield

Методика

A suspension of 2,3-Dihydro-2-oxo-1-phenyl-3-(4-pyridinylmethyl)-1H-indole-3-butanoic acid ethyl ester hydrochloride (10.0 g, 22.2 mmol) in 50 ml dry THF was treated with excess 1M BH3 -THF and stirred at room temperature for 3 days. The excess borane was decomposed with MeOH, and the mixture was concentrated in vacuo. The residue was digested with 100 ml 1N HCl for 3 hours at 80° C. , and the solution was concentrated. The residue was partitioned between 200 ml EtOAc and 100 ml 5% NaHCO3. The organic phase was washed with water and brine, dried over MgSO4, filtered, treated with 44 ml 1N HCl-Et2O, evaporated in vacuo. The residue was suspended in hot CH3CN and left standing overnight. The resulting crystals were collected by filtration, washed with Et2O, and dried to give the product in 30% (2.72 g) yield; mp 196°-197° C.; IR(nujol): OH @3356 cm-1 ; C=O @1709 cm -1 ; NMR(CDCl3TMS): δ1.13, 1.24 (2m, 2H, CH2 --C--CO), 2.51 (m, 2H, CH2 --CO), 2.1-3.0 (m, 2H, CH2 --C--C--CO), [3.40 (d, 1H, J=12.4 Hz), 3.54 (d, 1H, J=12.5 Hz), CH2 -Pyr], 3.48 (t, 2H, OCH2), [6.5 (m, 1H), 7.2 (m, 2H), 7.4 (m, 6H), Phe+1,2-Phe], [6.99 (d, 2H), 8.49 (d, 2H), 4-Pyr]; mass spec m/e 373(M+1); Anal calcd for C24H24N2O2HCl, MW 408.93: C, 70.49; H, 6.16; N, 6.85. Found: C, 70.44; H, 6.00; N, 6.67.

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