HCID 19787969, compound → HCID 19787965, compound

HRID 1656377Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:17]1[CH:16]=[N:15][C:14]([CH:32]=[O:33])=[C:13]([CH2:34][O:35][CH3:36])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]1([Li])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCCC1.CCOCC.CCCCCC.C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1)(=[O:24])=[O:23])[C:17]1[CH:16]=[N:15][C:14]([CH:32]([OH:33])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:13]([CH2:34][O:35][CH3:36])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of 1.0 g of 6-benzyloxy-3-formyl-4-methoxymethyl -9-(4-methylphenylsulfonyl)-beta-carboline in 60 ml of absolute tetrahydrofuran was mixed at -60° C. under argon with 2.4 ml of a 1.08 molar phenyllithium solution in ether/hexane, stirred for 1 hour at -60° C. and then heated slowly to room temperature. After taking up in ethyl acetate/water, the organic phase was separated, washed with saturated sodium chloride solution, dried and concentrated by evaporation. After column chromatography on silica gel with the eluants dichloromethane/ethanol 15:1 and cyclohexane/ethyl acetate 1:1, 717 mg of the title compound was obtained with melting point 169°-171° C.

Workup

temperatureheated slowly to room temperature
customthe organic phase was separated
washwashed with saturated sodium chloride solution
customdried
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-406a6d8800f04c5ebca8b0560ce87c18
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254563

Reaction notes

Loading…