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Ammonia → 1-Benzoyl-trans-3-amino-4-methylthio-pyrrolidine

HRID 265702
Notes
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Reaction equation

HRID 265702 reaction equation
[C:1]([N:9]1[CH2:13][CH:12]=[CH:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][S:15](Cl)(=O)=O.[NH3:19].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C(Cl)Cl>[C:1]([N:9]1[CH2:13][C@@H:12]([S:15][CH3:14])[C@H:11]([NH2:19])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 112522831H-Pyrrole, 1-benzoyl-2,5-dihydro-

Product 1

HCID 702820171-Benzoyl-trans-3-amino-4-methylthio-pyrrolidine

Reagents, catalysts & solvents 3

HCID 962Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

41.5 g (0.24 mol) of 1-benzoyl-2,5-dihydropyrrole are initially introduced into 240 ml of methylene chloride, and 24.8 g (0.3 mol) of methanesulphonyl chloride are added dropwise at 0° C. The mixture is subsequently stirred at room temperature for 16 hours, the solvent is then stripped off under 8 mbar and the residue is taken up in 240 ml of tetrahydrofuran. After addition of 65 g of 25% strength ammonia solution, the mixture is heated at 80° C. in an autoclave for 10 hours. It is then poured into 5 times the amount of water, the pH is brought to 10-11 with sodium carbonate, the mixture is extracted with methylene chloride and the extract is dried over sodium sulphate and concentrated. The crude product (50 g) is chromatographed on silica gel (mobile phase initially ethanol:ethyl acetate 1:3, then ethanol; Rf value: 0.34 ethanol).

Workup

  1. additionare added dropwise at 0° C
  2. temperaturethe mixture is heated at 80° C. in an autoclave for 10 hours
  3. extractionthe mixture is extracted with methylene chloride
  4. dry with materialthe extract is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product (50 g) is chromatographed on silica gel (mobile phase initially ethanol:ethyl acetate 1:3

Sources & evidence

ORD record
ord-3cd7799624fd4c2fb0848aab196067d2
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05648493

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes