(1S)-(+)-Camphor-10-sulphonic acid → (1R)-1'-{[1-(6-Phenylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 504285Notes

Reaction equation

HRID 504285 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3([C:16]([OH:18])=O)[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[NH:34]1[CH2:38][CH2:37][C@@:36]2([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[C:40](=[O:47])[O:39]2)[CH2:35]1>>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3([C:16]([N:34]4[CH2:38][CH2:37][C@@:36]5([C:42]6[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=6[C:40](=[O:47])[O:39]5)[CH2:35]4)=[O:18])[CH2:14][CH2:15]3)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 57989403(1R)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-oneHCID 66661648HCID 66661648, compound

Product 1

HCID 66662296(1R)-1'-{[1-(6-Phenylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Procedure

1-(6-Phenylpyridin-3-yl)cyclopropanecarboxylic acid was then coupled with (1S)-(+)-10-camphorsulfonic acid salt of (1R)-3H-spiro-[2-benzofuran-1,3′-pyrrolidin]-3-one using procedures analogous to those of Example 83 to afford (1R)-1′-{[1-(6-Phenylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one. MS (ESI): (M+H)+=411.1

Sources & evidence

ORD record
ord-b2901d20b4354ad88eace1593f496d7f
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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