Hydrogen Bromide → 9-Benzenesulfonyl-2,3,4,9-tetrahydro-1H-beta-carboline
Reaction equation
Br.C(OC([N:12]1[CH2:24][CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:14]=2[CH2:13]1)=O)C1C=CC=CC=1.C(OCC)C>C(O)(=O)C>[C:28]1([S:25]([N:15]2[C:14]3[CH2:13][NH:12][CH2:24][CH2:23][C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)(=[O:27])=[O:26])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1Participants
5
Procedure
33% hydrogen bromide in glacial acetic acid (20.7 ml) was added to a suspension of the product from stage 2 (4.14 g, 9.27 mmol) in glacial acetic acid (20.7 ml) and the mixture was stirred at room temperature for 1 h. The mixture was poured into diethyl ether (500 ml). The hydrobromide which had precipitated out was filtered off with suction, washed with diethyl ether and dried over potassium hydroxide in a desiccator. Saturated potassium carbonate solution (100 ml) was added to the salt (3.60 g) and the resulting mixture was extracted with methylene chloride (3×25 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.
Workup
- customThe hydrobromide which had precipitated out
- filtrationwas filtered off with suction
- washwashed with diethyl ether
- dry with materialdried over potassium hydroxide in a desiccator
- additionSaturated potassium carbonate solution (100 ml) was added to the salt (3.60 g)
- extractionthe resulting mixture was extracted with methylene chloride (3×25 ml)
- dry with materialThe combined organic phases were dried with sodium sulfate
- concentrationconcentrated i
Sources & evidence
- ORD record
- ord-de0878fcef444084879e659976b97936
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288406B2
Reaction notes
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