Borane;tetrahydrofuran → Benzyl 3-(aminomethyl)pyrrolidine-1-carboxylate

HRID 854311Notes

Reaction equation

HRID 854311 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([C:16](=O)[NH2:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 23577266HCID 23577266, compound

Product 1

HCID 15550581Benzyl 3-(aminomethyl)pyrrolidine-1-carboxylate

Procedure

A mixture of 1 g of 3-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester and 24 mL of 1M borane-THF was stirred at room temperature for 24 h, then quenched with 50 mL of 3N HCl. The mixture was concentrated under reduced pressure, followed by being partitioned between 50 mL chloroform and 25 mL saturated aqueous sodium carbonate. Concentration of the combined extracts after drying over magnesium sulfate gave the product as a resin:

Workup

  1. customquenched with 50 mL of 3N HCl
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customby being partitioned between 50 mL chloroform and 25 mL saturated aqueous sodium carbonate
  4. dry with materialConcentration of the combined extracts after drying over magnesium sulfate
  5. customgave the product as a resin

Sources & evidence

ORD record
ord-435b03bd49d74a2aa57e1eab939e611a
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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