(2S,4R)-1-Benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-methoxypyrrolidine → (2r,8As)-2-phenyl-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one

HRID 1245031Notes

Reaction equation

HRID 1245031 reaction equation
C(OC([N:11]1[CH2:15][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][C@H:12]1[CH2:22][C:23](=[O:30])[CH2:24][C:25](OCC)=O)=O)C1C=CC=CC=1.C(OC(N1C[C@H](OC)C[C@H]1CC(=O)CC(OCC)=O)=O)C1C=CC=CC=1>>[C:16]1([C@@H:14]2[CH2:15][N:11]3[C@H:12]([CH2:22][C:23](=[O:30])[CH2:24][CH2:25]3)[CH2:13]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 57501855(2S,4R)-1-Benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-methoxypyrrolidineHCID 57501856(2s,4r)-1-Benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-phenylpyrrolidine

Product 1

HCID 57457955(2r,8As)-2-phenyl-1,2,3,5,6,7,8,8a-octahydroindolizin-7-oneYield 27%

Procedure

In a similar manner to that described in Preparative Example 1(iii)′ above, a reaction was conducted, using (2S,4R)-1-benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-phenylpyrrolidine [obtained as described in Preparative Example 6(iv)′ above] instead of (2S,4R)-1-benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-methoxypyrrolidine, to give the title compound as a pale yellow oil (yield: 27%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-64d68903b31d4c3e9ce3bbf89b9773b2
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

Loading…