Potassium Carbonate → methyl 4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]methyl}benzoate

HRID 732639Notes

Reaction equation

HRID 732639 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.[C:19]1([C@H:29]([N:31]([CH2:39][C@@H:40]2[C@@H:44]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:43][NH:42][CH2:41]2)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH3:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>CC(C)=O>[C:34]([O:33][C:32]([N:31]([CH2:39][C@@H:40]1[C@@H:44]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH2:43][N:42]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH2:41]1)[C@@H:29]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:30])=[O:38])([CH3:35])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate

Product 1

HCID 68913897methyl 4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate and methyl 4-(bromomethyl)benzoate were added in that order to an acetone solution of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate and stirred at room temperature for 20Hours. Thereafter, work-up and purification were carried out in the standard method to obtain methyl 4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin 1-yl]methyl}benzoate. FP: 579.

Workup

  1. customThereafter, work-up and purification

Sources & evidence

ORD record
ord-8ec75f5ef2014959962b562977bf1612
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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