Dichloromethane → Ethyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(Cl)Cl.[C:10]1([C@H:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][NH:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(N(CC)CC)C>[C:10]1([C@H:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][N:17]2[C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
5
Conditions
- Temperature
- 27.5 °C
Procedure
Ethyl chloroformate (5.61 g) was slowly added to a mixture of methylene chloride (100 ml), (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (10 g) and triethylamine (5.32 g) at 5-15° C. over a period of 30 min. Thereafter, the reaction mass was warmed to 25-30° C. and stirred at 25-30° C. for 1 h. The reaction solution was sequentially washed with water (50 ml), 3% w/w hydrochloric acid (50 ml), water (50 ml) and 5% w/w aqueous sodium chloride (50 ml) at 25-30° C. The solvent was removed under reduced pressure at 30-40° C. to produce (1S)-ethyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate (13.0 g) as a pale yellow oil. Chromatographic Purity (By HPLC): 99.22%.
Workup
- customThereafter, the reaction
- washThe reaction solution was sequentially washed with water (50 ml), 3% w/w hydrochloric acid (50 ml), water (50 ml) and 5% w/w aqueous sodium chloride (50 ml) at 25-30° C
- customThe solvent was removed under reduced pressure at 30-40° C.
Sources & evidence
- ORD record
- ord-f1e047386d9b4c9fa4484b6b427ef15c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772491B2
Reaction notes
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