Water → HCID 54394851, compound
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.CN.[Li].O>O1CCCC1.C(O)CCC>[CH2:1]1[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
Typically, the tetrahydroisoquinoline was suspended or dissolved in a cosolvent such as tetrahydrofuran ort-butyl alcohol. This mixture was cooled to −10° C. and methylamine was added and the temperature was maintained at −10° C. The lithium metal was charged in portions and the reaction mixture was stirred at −10° C. for another 30 minutes to about 2 hours after sufficient lithium metal was charged. The reaction mixture was warmed to room temperature and then added to water to produce the product hexahydroisoquinoline as a precipitate.
Workup
- temperaturethe temperature was maintained at −10° C
- additionwas charged
- temperatureThe reaction mixture was warmed to room temperature
Sources & evidence
- ORD record
- ord-f6e4fea84d0f48fba3a8d64dd7fe1dc4
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08227611B2
Reaction notes
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