Lithium Hydroxide → (1R)-1'-{[1-(6-pyrrolidin-1-ylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one

HRID 969087Notes

Reaction equation

HRID 969087 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]3([C:15]([O:17]CC)=O)[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl.Cl.[NH:24]1[CH2:28][CH2:27][C:26]2([C:36]3[CH:35]=[CH:34][N:33]=[CH:32][C:31]=3[C:30](=[O:37])[O:29]2)[CH2:25]1>CO>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]3([C:15]([N:24]4[CH2:28][CH2:27][C@@:26]5([C:36]6[CH:35]=[CH:34][N:33]=[CH:32][C:31]=6[C:30](=[O:37])[O:29]5)[CH2:25]4)=[O:17])[CH2:13][CH2:14]3)=[CH:8][CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 66661814Ethyl 1-(6-pyrrolidin-1-ylpyridin-3-yl)cyclopropanecarboxylateHCID 666621753H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one dihydrochloride

Product 1

HCID 66662063(1R)-1'-{[1-(6-pyrrolidin-1-ylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above material of ethyl 1-(6-pyrrolidin-1-ylpyridin-3-yl)cyclopropanecarboxylate was treated with LiOH in methanol to afford the corresponding acid, which was then coupled with 3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one dihydrochloride using procedures analogous to those for example 96 to afford (1R)-1′-{[1-(6-pyrrolidin-1-ylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one. MS (ESI): (M+H)+=405.1

Workup

  1. customto afford the corresponding acid, which

Sources & evidence

ORD record
ord-0931f803d5a4444f9d01826e6fea6bee
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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