Pyridine → 4-(methoxycarbonyl)phenyl (3R,4S)-3-({(tert-butoxycarbonyl) [(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

HRID 732641Notes

Reaction equation

HRID 732641 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=[O:9].[C:21]1([C@H:31]([N:33]([CH2:41][C@@H:42]2[C@@H:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:45][NH:44][CH2:43]2)[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH3:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:36]([O:35][C:34]([N:33]([CH2:41][C@@H:42]1[C@@H:46]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:45][N:44]([C:8]([O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[O:9])[CH2:43]1)[C@@H:31]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)[CH3:32])=[O:40])([CH3:37])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 854163Methyl 4-[(chlorocarbonyl)oxy]benzoateHCID 86628525HCID 86628525, compound

Product 1

HCID 689143824-(methoxycarbonyl)phenyl (3R,4S)-3-({(tert-butoxycarbonyl) [(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0.06 ml portion of pyridine and 103 mg of methyl 4-[(chlorocarbonyl)oxy]benzoate (mfd. by Fluka) were added in that order to a THF (5.0 ml) solution of 173 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate and stirred for 1 week. Thereafter, its work-up and purification were carried out in the standard method to obtain 4-(methoxycarbonyl)phenyl (3R,4S)-3-({(tert-butoxycarbonyl) [(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as a crude product. FP: 609.

Workup

  1. customThereafter, its work-up and purification

Sources & evidence

ORD record
ord-2f687eb6cf704cceba5e94fc7c2b7565
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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