(+)-(1R)-1-[2-(Diphenylphosphino)-1-naphthalenyl]quinoline → HCID 67304901, compound

HRID 1009829Notes

Reaction equation

HRID 1009829 reaction equation
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CN=2)C2C=CC=CC=2)=CC=1.[CH:34]([O:37][C:38]([C@@H:40]1[CH2:44][C@H:43]([C:45](=[O:47])[CH3:46])[C@H:42]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH2:57][CH2:58][CH2:59][O:60][CH3:61])[CH:49]=2)[NH:41]1)=[O:39])([CH3:36])[CH3:35]>>[CH:34]([O:37][C:38]([C@H:40]1[CH2:44][C@@H:43]([C:45](=[O:47])[CH3:46])[C@@H:42]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH2:57][CH2:58][CH2:59][O:60][CH3:61])[CH:49]=2)[NH:41]1)=[O:39])([CH3:35])[CH3:36]

Participants

3

Reactant 2

HCID 4379935(+)-(1R)-1-[2-(Diphenylphosphino)-1-naphthalenyl]quinolineHCID 67305052HCID 67305052, compound

Product 1

HCID 67304901HCID 67304901, compound

Procedure

In a similar fashion using (R)-QUINAP, (2S,4S,5R)-4-Acetyl-5-[4-methoxy-3-(3-methoxypropoxy)-phenyl]-pyrrolidine-2-carboxylic acid isopropyl ester, 1H-NMR, δ CDCl3: 6.89-6.79 (3H, m, Ph), 5.15 (1H, m, CHO), 4.52 (1H, d, PHCHN), 4.11 (2H, t, CH2O), 3.85 (3H, s, MeO), 3.60 (2H, t, CH2O), 3.41 (1H, m, CHCO), 3.48 (3H, s, MeO), 2.39 (1H, ddd, CH), 2.29 (1H, ddd, CH), 2.12 (2H, m, CH2), 1.30 (6H, 2 overlapping d, 2×Me), can be prepared. The epimer (2R,4R,5S)-4-Acetyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-2-carboxylic acid isopropyl ester, can also be isolated; 1H-NMR, δ CDCl3: 6.89-6.79 (3H, m, Ph), 5.15 (1H, m, CHO), 4.52 (1H, d, PHCHN), 4.11 (2H, t, CH2O), 3.85 (3H, s, MeO), 3.60 (2H, t, CH2O), 3.41 (1H, m, CHCO), 3.48 (3H, s, MeO), 2.39 (1H, ddd, CH), 2.29 (1H, ddd, CH), 2.12 (2H, m, CH2), 1.30 (6H, 2 overlapping d, 2×Me).

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-b78a2ec211c84a28b17aac8eecb3c912
Source dataset
uspto-grants-2011_07
Patent number
US07973175B2

Reaction notes

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