Acetonitrile → HCID 86628557, compound

HRID 732697Notes

Reaction equation

HRID 732697 reaction equation
[C:1]1([C@H:11]([N:13]([CH2:21][C@@H:22]2[C@@H:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][NH:24][CH2:23]2)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([N:35](CC)CC)C.CC#N.[N+](C1C=CC([O:50][C:51]([O:53][C:54]2[CH:63]=[CH:62][CH:61]=[CH:60][C:55]=2[C:56]([O:58][CH3:59])=[O:57])=O)=CC=1)([O-])=O>C(OCC)(=O)C>[C:16]([O:15][C:14]([N:13]([CH2:21][C@H:22]1[C@@H:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:25][N:24]([NH:35][C:51]([O:53][C:54]2[CH:63]=[CH:62][CH:61]=[CH:60][C:55]=2[C:56]([O:58][CH3:59])=[O:57])=[O:50])[CH2:23]1)[C@@H:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:12])=[O:20])([CH3:18])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 66603210HCID 66603210, compoundHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate

Product 1

HCID 86628557HCID 86628557, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 223 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate, 78.6 mg of triethylamine and 4.5 ml of MeCN was mixed, under ice-cooling, with 215 mg of methyl 2-{[(4-nitrophenoxy)carbonyl]oxy}benzoate and stirred at room temperature for 4Hours. The reaction solution was mixed with ethyl acetate, washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order and dried with anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate) to obtain 189 mg of 2-(methoxycarbonyl)phenyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carbamate as a white amorphous substance.

Workup

  1. additionwas mixed, under ice-
  2. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-194549a8ae26406a9b6f2647a68351fe
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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