(Pyrrolidin-3-yl)methanol → benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 341802

Reaction equation

HRID 341802 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:8]([O:15][C:16]([NH:18][C:19](=[NH:22])OC)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][C:16]([NH:18][C:19]([N:5]1[CH2:6][CH2:7][CH:3]([CH2:2][OH:1])[CH2:4]1)=[NH:22])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 13400657(Pyrrolidin-3-yl)methanolHCID 139267837benzyl N-(C-methoxycarbonimidoyl)carbamate

Product 1

HCID 140379085benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamateYield 25.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

1.01 g (0.01 mole) (3RS)-3-hydroxymethyl pyrrolidine and 2.29 g (0.011 mole) N-benzyloxycarbonyl-O-methylisourea was dissolved (the amine not very soluble) in toluene and heated to 60° C. for three hours followed by stirring at room temperature over night. The mixture was evaporated and the 1H-NMR showed that the reaction was not completed. The mixture was therefore dissolved in 15 ml acetonitrile and heated to 60° C. for three hours followed by stirring at room temperature over night. The solvent was evaporated and the mixture was dissolved in CH2Cl2, washed once with water, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2 /MeOH 95/5 as eluent to yield 0.70 g (25%) of the product.

Workup

  1. customThe mixture was evaporated
  2. dissolutionThe mixture was therefore dissolved in 15 ml acetonitrile
  3. temperatureheated to 60° C. for three hours
  4. stirringby stirring at room temperature over night
  5. customThe solvent was evaporated
  6. dissolutionthe mixture was dissolved in CH2Cl2
  7. washwashed once with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5b550e99bd8a4e83aecd2baa957c8fb1
Source dataset
uspto-grants-1999_01
Patent number
US05856307

Linked notes

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