1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline → 1-(3,4-Methylenedioxyphenyl)-2-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-1H-beta-carboline
Reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][NH:11]3)=[CH:4][C:3]=2[O:2]1.[C:23]([O:27][C:28](OC([O-])=O)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(OC([O-])=O)(=O)[O-]>CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])=[CH:4][C:3]=2[O:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (27.7 g, 94.8 mmol) (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24) in dry methanol (300 mL) was added t-butylpyrocarbonate (25.0 g, 114 mmol). Shortly after the addition of the pyrocarbonate, a clear solution was formed. The solution was stirred at ambient temperature for 1 h, resulting in formation of a white precipitate. The solid was collected by filtration, washed with a 1:1 mixture of diethyl ether:pentane, and dried in vacuo to yield the product as a white solid.
Workup
- customprepared
- customa clear solution was formed
- customresulting in formation of a white precipitate
- filtrationThe solid was collected by filtration
- washwashed with a 1:1 mixture of diethyl ether
- dry with materialpentane, and dried in vacuo
Sources & evidence
- ORD record
- ord-4298f74ddd204e0da772528851b793e2
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06818646B2
Reaction notes
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