Triethylamine → (2S,4R)-2-Methyl 1-(4-nitrobenzyl) 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 1034478Notes

Reaction equation

HRID 1034478 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])=[O:4].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(OCC)(=O)C>ClCCl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:7][N:6]1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)=[O:12])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 18656014(2S, 4R)-4-hydroxy-N-(4-nitrobenzyloxycarbonyl)proline methyl ester

Product 1

HCID 57030081(2S,4R)-2-Methyl 1-(4-nitrobenzyl) 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-p-nitrobenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (59.44 g: 0.183 mole) in dichloromethane (150 ml) stirring at -20° C., triethylamine (30.5 ml: 1.2 eq.) and methanesulfonyl chloride (17 ml: 1 eq.) are added. The mixture is stirred at the same temperature for 35 minutes. To the mixture is added ice water and ethyl acetate. The organic layer is taken, washed with water, dried over magnesium sulfate, and concentrated in vacuo to give (2S,4R)-1-p-nitrobenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester (74.05 g). Yield: Quantitative. NMR δ(CDCl3) ppm: 2.20 to 2.42(m, 1H), 2.55 to 2.85(m, 1H), 3.07(s, 3H), 3.67(s, 1.5H), 3.78(s, 1.5H), 3.80 to 4.05(m, 2H), 4.53(t, J=7 Hz, 1H), 5.06 to 5.40(m, 3H), 7.47(d, J=9 Hz, 1H), 7.51(d, J=9 Hz, 1H), 8.23(d, J=9 Hz, 2H). IR ν (CHCl3) cm-1 : 1748, 1712, 1608.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fecb2d28bd14e20b9df6f1191e680b1
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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