Dichloromethane → 3-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

HRID 732700Notes

Reaction equation

HRID 732700 reaction equation
ClCCl.O=C1CCC(=O)N1[O:11][C:12]([O:14][CH2:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=O.OCC(C)(C)C(OC)=O.[C:32]1([C@H:42]([N:44]([CH2:52][C@@H:53]2[C@@H:57]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:56][NH:55][CH2:54]2)[C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH3:43])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1>C(N(CC)CC)C>[C:47]([O:46][C:45]([N:44]([CH2:52][C@@H:53]1[C@@H:57]([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH2:56][N:55]([C:12]([O:14][CH2:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[O:11])[CH2:54]1)[C@@H:42]([C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1)[CH3:43])=[O:51])([CH3:49])([CH3:50])[CH3:48]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 84152Methyl 3-hydroxypivalateHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamateHCID 86628559HCID 86628559, compound

Product 1

HCID 866285583-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 2 ml dichloromethane solution of methyl 3-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)-2,2-dimethylpropionate prepared from 136 mg of methyl 3-hydroxy-2,2-dimethylpropionate in the same manner as in Reference Example 46 was added to 5 ml dichloromethane solution of 235 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate and 0.21 ml of triethylamine. After 12Hours of stirring at room temperature, the reaction solution was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate) to obtain 227 mg of 3-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as a colorless amorphous substance.

Workup

  1. concentrationthe reaction solution was concentrated under a reduced pressure
  2. customthe thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-862bb5e985b24741848c401502531de8
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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