Sodium Hydroxide → (R)-3-(4-chlorophenyl)-1-(phenylmethyl)hexahydropyrazine dihydrochloride
Reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12][N:11]2CC=C)=[CH:6][CH:5]=1.[OH-].[Na+]>[Ru](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[NH:11][CH2:12][CH2:13][N:14]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15]2)=[CH:8][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Mixed were (R)-2-(4-Chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride (104 mg, 0.25 mmol) produced in Example 18 and ruthenium chloride (3 mg, 0.04 mmol). The mixture was stirred at 100° C. for 24 hours. To the mixture, 30 wt % aqueous solution of sodium hydroxide (85 mg, 2.5 equivalents) and toluene (2 mL) were added. The formed insolubles were separated by filtration, and washed with distilled water (2 mL) and toluene (2 mL). After the organic layer and aqueous layer of the filtrate were separated, the organic layer was washed twice with distilled water (4 mL). The obtained organic layer was concentrated and dried under vacuum, to obtain 68 mg of the crude product of the title compound as pale brown oil (yield: 87%, chemical purity: 93.5 area %, optical purity: 98.1% e.e.). The retention time in the chemical purity analysis method was 3.1 min.
Workup
- additionMixed
- customThe formed insolubles were separated by filtration
- washwashed with distilled water (2 mL) and toluene (2 mL)
- customAfter the organic layer and aqueous layer of the filtrate were separated
- washthe organic layer was washed twice with distilled water (4 mL)
- concentrationThe obtained organic layer was concentrated
- customdried under vacuum
Sources & evidence
- ORD record
- ord-6b48065f8e2b4c9cb5da246eaee62ab6
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273883B2
Reaction notes
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