Methanol → methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([OH:13])=[O:12])[NH:2]1.S(Cl)([Cl:16])=O.[CH3:18]O>>[ClH:16].[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([C:11]([O:13][CH3:18])=[O:12])[NH:2]1Participants
Procedure
In succession 5 g of tetrahydroisoquinoline 3-carboxylic acid and 30 ml of methanol are introduced into a three-necked flask. 6 g of thionyl chloride are added to this suspension by pouring carefully, taking care that the temperature does not exceed 0°+5°. The addition takes approximately 10 minutes. After the addition is completed, stirring is continued for 2 hours at room temperature, and then the mixture is heated to reflux for 11/2 hours. Once the mixture has dissolved completely, heating is discontinued and the mixture is then evaporated to dryness. The residue is taken up three times in methanol and then evaporated to dryness. Finally, 8 g of colourless crystals are obtained and purified by trituration with ether. The crystals are separated off by filtration, washed with ether and dried. 6.4 g of methyl tetrahydroisoquinoline-3-carboxylate hydrochloride are thus obtained.
Workup
- additionby pouring carefully
- customdoes not exceed 0°
- custom5°
- additionThe addition
- additionAfter the addition
- waitis continued for 2 hours at room temperature
- temperaturethe mixture is heated
- temperatureto reflux for 11/2 hours
- dissolutionOnce the mixture has dissolved completely
- temperatureheating
- customthe mixture is then evaporated to dryness
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-03ad1612f3c5474cb4d63101f4466441
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04565819
Reaction notes
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