Triethylamine → (3R*,4S*) N,N-Dimethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide
Reaction equation
Cl.[C:2]1([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]2[N:14]3[CH2:15][CH2:16][C@@H:11]([C@@H:12]([C:17](O)=[O:18])[CH2:13]3)[C:10]2=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:28][NH:29][CH3:30].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:28][N:29]([CH3:30])[C:17]([C@@H:12]1[C@@H:11]2[CH2:16][CH2:15][N:14]([CH:9]([CH:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:10]2=[O:20])[CH2:13]1)=[O:18]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 46 (2.1 g, 6.6 mmol) and dimethylamine hydrochloride (0.65 g, 8.0 mmol) in DMF (30 ml) was treated with triethylamine (1.3 g, 13 mmol) at room temperature. To this suspension was added diethyl cyanophosphonate (1.2 g, 7.3 mmol) followed by triethylamine (0.67 g, 6.7 mmol) at room temperature. The mixture was stirred at room temperature for 5 hours, poured into NaHCO3 aq (50 ml) and extracted with EtOAc three times. The combined extracts were dried over Na2SO4 and concentrated. This mixture was purified by a column chromatography on silica gel (hexane:EtOAc=1:4) to give 47 as a single isomer at 3-position (1.4 g, 3.9 mmol, 60%)
Workup
- extractionextracted with EtOAc three times
- dry with materialThe combined extracts were dried over Na2SO4
- concentrationconcentrated
- customThis mixture was purified by a column chromatography on silica gel (hexane:EtOAc=1:4)
Sources & evidence
- ORD record
- ord-530303c6fce344d68ba01f328f6f3c98
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716965
Reaction notes
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