Diisopropylethylamine → 1'-{[1-(4-Phenoxyphenyl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one

HRID 969092Notes

Reaction equation

HRID 969092 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]([OH:19])=O)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[NH:22]1[CH2:26][CH2:25][C:24]2([C:34]3[CH:33]=[CH:32][N:31]=[CH:30][C:29]=3[C:28](=[O:35])[O:27]2)[CH2:23]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2([C:17]([N:22]3[CH2:26][CH2:25][C:24]4([C:34]5[CH:33]=[CH:32][N:31]=[CH:30][C:29]=5[C:28](=[O:35])[O:27]4)[CH2:23]3)=[O:19])[CH2:15][CH2:16]2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 666617771-(4-Phenoxyphenyl)cyclopropanecarboxylic acidHCID 666621753H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one dihydrochloride

Product 1

HCID 666622981'-{[1-(4-Phenoxyphenyl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-phenoxyphenyl)cyclopropanecarboxylic acid (15 mg, 0.059 mmol), 3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one dihydrochloride (16 mg, 0.059 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (27.4 mg, 0.062 mmol), and N,N-diisopropylethylamine (36 ul, 0.21 mmol) in N,N-dimethylformamide (1 ml) was stirred at room temperature for 4 hours. The desired product then was obtained from the mixture by prep-HPLC (6.2 mg, 25%). LCMS: m/z 427.1 (M+H)+; 449.1 (M+Na)+.

Sources & evidence

ORD record
ord-e46f57a2397f4ad6b4cb61949425b349
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

Loading…