Methanol → 5-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-methanol

HRID 1720328Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=O)C.[H-].C([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[C:17]2[C:18]([CH2:19][O:20][CH3:21])=[C:6]([CH2:4][OH:3])[N:7]=[CH:8][C:9]=2[NH:10]3)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: -75 °C

Procedure

0.5 g (0.00122 mol) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is dissolved in 13 ml of toluene. To the solution cooled to -75° C. 2.3 ml of a 1,2-molar solution of diisobutylaluminiumhydride in toluene is slowly instilled under argon. It is stirred for 10 minutes more at -75° C., then for one hour at room temperature. 0.9 ml of methanol is slowly instilled to the reaction mixture again cooled to -75° C., it is stirred 10 minutes more, then 1.5 ml of a saturated potassium sodium tartrate solution is instilled. It is stirred for 20 minutes more at room temperature, then the mixture is extracted with ethyl acetate. The combined extracts are dried and concentrated by evaporation, the residue is recrystallized from ethanol. Thus 0.09 g (20% of theory) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-methanol is obtained, melting point 220°-222° C.

Workup

waitfor one hour at room temperature
temperatureagain cooled to -75° C.
stirringit is stirred 10 minutes more
stirringIt is stirred for 20 minutes more at room temperature
extractionthe mixture is extracted with ethyl acetate
customThe combined extracts are dried
concentrationconcentrated by evaporation
customthe residue is recrystallized from ethanol

Sources & evidence

ORD record: ord-5178403720bc4166b5eea24cfa6413a0
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506234

Reaction notes

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