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

HRID 259998Notes

Reaction equation

HRID 259998 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:20]([O:22][CH3:23])=[O:21])[CH2:3]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>ClCCl>[CH3:31][S:32]([O:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])[C@H:4]([C:20]([O:22][CH3:23])=[O:21])[CH2:3]1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 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 crude (2S,4R)-4-hydroxy-2-methoxycarbonyl-1-p-nitrobenzyloxycarbonylpyrrolidine (86.1 g) in dichloromethane (1 liter) under ice cooling are added triethylamine (52 ml) and then methanesulfonyl chloride (21.6 ml), and the mixture is stirred for 25 minutes. The reaction mixture is acidified with diluted hydrochloric acid and stirred. The organic layer is taken, washed with aqueous sodium hydrogen carbonate and water, dried over sodium sulfate, and concentrated in vacuo to give (2S,4R)-4-methanesulfonyloxy-2-methoxycarbonyl-1-p-nitrobenzyloxycarbonylpyrrolidine (2: 90.0 g) as an organge oil. This product can be used in the next step without further purification. IR ν (CHCl3) cm-1 : 1741, 1703, 1602. 1HNMR δ (CDCl3) ppm: 2.22 to 2.82(2H, m), 3.07(3H, s), 3.67, 3.78(3H, 2s), 3.75 to 4.03(2H, m), 4.55(1H, t, J=7.8 Hz), 5.08 to 5.39(3H, m), 7.43 to 7.58(2H, m), 8.23(2H, d, J= 8.6 Hz).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd5fb0d1183046e19f9c132aaa2bbd5e
Source dataset
uspto-grants-1996_06
Patent number
US05523415

Reaction notes

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