反应详情

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.

1. concentrationthe mixture was concentrated in vacuo
2. waitThe residue was digested with 100 ml 1N HCl for 3 hours at 80° C.
3. concentrationthe solution was concentrated
4. customThe residue was partitioned between 200 ml EtOAc and 100 ml 5% NaHCO3
5. washThe organic phase was washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. additiontreated with 44 ml 1N HCl-Et2O
9. customevaporated in vacuo
10. waitleft
11. waitstanding overnight
12. filtrationThe resulting crystals were collected by filtration
13. washwashed with Et2O
14. customdried
15. customto give the product in 30% (2.72 g)
16. customyield