Benzoic Acid → (7S,8aS)-2-(5-Chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-7-yl benzoate
Reaction equation
[OH:1][C@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=3)[CH2:9][C@@H:4]2[CH2:3]1.[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:18]([O:1][C@@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=3)[CH2:9][C@@H:4]2[CH2:3]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 0.595 g (2.35 mmol) of (7R,8aS)-7-hydroxy-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 17), 0.430 g (3.52 mmol) of benzoic acid and 0.738 g (2.81 mmol) of triphenylphosphine in 25 mL of dry THF was treated with 0.44 mL (2.8 mmol) of diethyl azodicarboxylate, and the mixture stirred at ambient temperature for 16 h. The solvent was evaporated and the residue purified by flash silica gel chromatography with 10:1 methylene chloride:acetone. A second chromatography of the major fraction with the same system gave 0.63 g (75%) of the title compound. mp (.HCl) 202°-205° C. HRMS calcd for C19H21 ClN3O2 (MH+): 358.1322, found: 358.1320.
Workup
- customThe solvent was evaporated
- customthe residue purified by flash silica gel chromatography with 10:1 methylene chloride
Sources & evidence
- ORD record
- ord-a86f25b0cb43495ba8db6a0bd329ae6b
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05714487
Reaction notes
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