(2S,4R)-1-[(benzyloxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid → (8aS)-2,2-Difluoro-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one

HRID 1245027Notes

Reaction equation

HRID 1245027 reaction equation
[CH2:1]([O:4]C(N1CC=C(C2C(C3C=CN=C(F)C=3)=C(C3C=CC(F)=CC=3)NC=2)CC1)=O)[CH:2]=C.C(O[C:40]([N:42]1[CH2:49][C:48]([F:51])([F:50])[CH2:47][C@H:43]1[C:44](O)=O)=O)C1C=CC=CC=1.C(OC(N1C[C@H](OC)C[C@H]1C(O)=O)=O)C1C=CC=CC=1>>[F:51][C:48]1([F:50])[CH2:49][N:42]2[C@@H:43]([CH2:44][C:1](=[O:4])[CH2:2][CH2:40]2)[CH2:47]1

Participants

4

Reactant 3

HCID 12849521(2S,4R)-1-[(benzyloxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acidHCID 219226854-(1-Allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)-1H-pyrroleHCID 53909714(S)-1-((Benzyloxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 57457954(8aS)-2,2-Difluoro-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one

Procedure

In a similar manner to the procedures described in Preparative Examples 1(i)′, (ii) and (iii) above, reactions were carried out successively, using (2S)-1-benzyloxycarbonyl-4,4-difluoroproline as a starting material instead of (2S,4R)-1-benzyloxycarbonyl-4-methoxyproline, to give the title compound as a pale yellow oil (total yield for the 3 steps: 14%).

Sources & evidence

ORD record
ord-4d33df723ad049658393bd644b36894e
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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