Pyrrolidine → HCID 178472838, compound

HRID 1155239Notes

Reaction equation

HRID 1155239 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][P:8](Cl)(Cl)=[O:9])[CH3:2].[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>C(OCC)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:7]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[PH2:8]=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 12791028HCID 12791028, compound

Product 1

HCID 178472838HCID 178472838, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

Freshly prepared ethyl-N-[(benzylthio)carbonyl]-N-[dichlorophosphinylmethyl]-glycinate (12.55 g.; 0.033mol.) dissolved in 100 ml. of diethyl ether was added to a solution of pyrrolidine (9.3 g.; 0.13 mol.) in 100 ml. of diethyl ether. The reaction mixture was stirred for 16 hours at 25° C., then filtered. The filtrate was washed with water, dried with magnesium sulfate and concentrated in vacuo. To remove any remaining solvent, the residue was concentrated at 25° C. and 0.05 mm. to yield ethyl-N-[(benzylthio)carbonyl]-N-[bis(pyrrolidyl)-phosphinylmethyl]-glycinate, hemi-hydrate as an oil (nD25 =1.5424) having the following analysis:

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customTo remove any remaining solvent
  6. concentrationthe residue was concentrated at 25° C.

Sources & evidence

ORD record
ord-3f61dcde89da4e73be14d03e3f18069b
Source dataset
uspto-grants-1981_11
Patent number
US04300942

Reaction notes

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