Reaction equation
[N:1]1[CH2:5][CH2:4][CH2:3][CH:2]=1.[P:6]([O-:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.P(C1CCCN1)(=O)=O.N1CCC[C@H]1C(O)=O.C[C@H](NC([C@H]1N(C([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](N)CC(O)=O)=O)CCCNC(N)=N)=O)C(C)C)=O)CC2C=CC(O)=CC=2)=O)C(C)C)=O)CC2NC=NC=2)=O)CCC1)=O)C(O)=O>>[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[P:6]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:21])[O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
Conditions
- Temperature
- 85 °C
Procedure
This compound was synthesized from 1-pyrroline trimer (Nomura, Y., Ogawa, K., Takeuchi, Y., Tomoda, S., One Step Synthesis and Structural Confirmation with 1-Pyrroline Trimer, Chem. Lett. 1977, 693-696) and diphenyl phosphite using the procedure previously described for the synthesis of the diethyl ester (Petrillo, E. W., Spitzmiller, E. R., Synthesis of 2-Phosphopyrrolidine and Its Substitution for Proline in an Inhibitor of Angiotensin-Converting Enzyme, Tet. Lett. 1979, 51, 4929). A mixture of 1-pyrroline trimer (17 mmol, 3.5 g) and diphenyl phosphite (50 mmol, 11.7 g) was heated at 85° C. for 1.5 h under argon to give crude diphenyl pyrrolidine-2-phosphonate which was dissolved in 100 ml of dry diethyl ether, filtered and saturated with dry gaseous HCl. The precipitated hydrochloride 1 was collected by filtration, washed with ether and recrystallized from acetone, to give the pure product as a white solid in 49% yield: mp 146°-148° C.; 1H-NMR (D2O) δ(ppm): 2.0-2.5 (m, 4H), 3.40 (m, 2H), 4.25 (m, 1H), 6.90-7.30 (m, 10H); MS (FAB) m/e 304 (M-Cl)30. Anal. (C16H19NO3PCl): C, H, N, Cl.
Sources & evidence
- ORD record
- ord-34715100336a453da7c90c0485db0489
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05543396
Linked notes
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