1-(2-Hydroxyethyl)piperazine → (2S,4R)-2-[4-(2-Hydroxyethyl)-1-piperazinylcarbonyl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxy-carbonyl)pyrrolidine

HRID 727674Notes

Reaction equation

HRID 727674 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C.[CH3:27][S:28]([O:31][C@H:32]1[CH2:36][N:35]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=2)=[O:38])[C@H:34]([C:50](O)=[O:51])[CH2:33]1)(=[O:30])=[O:29]>C(#N)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:50]([C@@H:34]2[CH2:33][C@@H:32]([O:31][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:36][N:35]2[C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=2)=[O:38])=[O:51])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 13502650trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 86752003(2S,4R)-2-[4-(2-Hydroxyethyl)-1-piperazinylcarbonyl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxy-carbonyl)pyrrolidineYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.11 g of 1-(2-hydroxyethyl)piperazine, 1.29 ml of diethyl cyanophosphonate and 1.18 ml of triethylamine were added, in that order, whilst ice-cooling, to a solution of 3.00 g of trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline [prepared as described in step 54(a)(i) above] in 35 ml of dry acetonitrile, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 2.60 g of the title compound, as a powder.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-caa7f5bf6a0446e393ca37a879f52b25
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

Loading…