Dimethylformamide → (R)-Cyclohexyl-[(3S,4S)-3-(4-imidazo[4,5-b]pyridin-3-yl-piperidin-1-ylmethyl)-4-phenyl-pyrrolidin-1-yl]-acetic acid

HRID 1068171Notes

Reaction equation

HRID 1068171 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]([O:17]CC2C=CC(OC)=CC=2)=[O:16])[CH2:4]1)=O.[NH:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:43]3C=[CH:45][C:46](F)=[CH:47][C:42]=3[N:41]=[CH:40]2)[CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C[N:64](C=O)C>C1COCC1>[N:41]1[C:42]2[C:43](=[N:64][CH:45]=[CH:46][CH:47]=2)[N:39]([CH:36]2[CH2:35][CH2:34][N:33]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:6][N:5]([C@H:14]([CH:27]4[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]4)[C:15]([OH:17])=[O:16])[CH2:4]3)[CH2:38][CH2:37]2)[CH:40]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 5049666Sodium triacetoxyborohydrideHCID 211931111-Piperidin-4-yl-5-fluoro-1-H-benzoimidazoleHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 20664163(R)-Cyclohexyl-[(3S,4S)-3-(4-imidazo[4,5-b]pyridin-3-yl-piperidin-1-ylmethyl)-4-phenyl-pyrrolidin-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 60 mg of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (prepared above as Aldehyde 5), 60 mg 1-piperidin-4-yl-5-fluoro-1-H-benzoimidazole (from Step D ) and 75 mg of sodium triacetoxyborohydride in 4 mL of THF and 1 mL of DMF, using a procedure analogous to that described in Example 95, Step D to provide 48 mg of the title compound as an oil.

Sources & evidence

ORD record
ord-c0f9602127ff4b0fb102bb5479b5dd8a
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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