Hydrochloric Acid → HCID 66781969, compound
Reaction equation
Cl.[C:2]1([C@H:8]([NH:10][C@H:11]([CH3:22])[CH2:12][C:13]2[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:21][CH2:20][CH2:19][C:15]1[CH:14]=[C:13]([CH2:12][C@H:11]([NH:10][C@@H:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:9])[CH3:22])[CH:18]=[CH:17][CH:16]=1Participants
Procedure
To a stirred solution of {3-[(R)-2-((R)-1-phenylethylamino)propyl]phenyl}-acetonitrile hydrochloride salt (2.00 g, 6.35 mmol) and cobalt(II) chloride hexahydrate (4.27 g, 18.0 mmol) in MeOH (40.0 mL) at 0° C. was added sodium tetrahydroborate (2.72 g, 71.8 mmol) portion-wise (reaction was exothermic). The reaction mixture was stirred for 1 h at room temperature and then concentrated aqueous hydrochloric acid was added and stirring was continued until the solid that had formed was broken-up. The mixture was then made basic by addition of aqueous sodium hydroxide (1 M). This mixture was filtered and the filtrate was extracted with DCM (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which as used in the next reaction without further purification.
Workup
- stirringstirring
- customthat had formed
- filtrationThis mixture was filtered
- extractionthe filtrate was extracted with DCM (50 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-09ab6a9c2dd44408b4cd8c90a78e6b66
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816088B2
Reaction notes
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