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

HRID 1827185Notes

Reaction equation

HRID 1827185 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 3-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester and 24 mL 1M borane-THF was stirred at room temperature for 24 h, then carefully quenched with 50 mL of 3N HCl. The mixture was concentrated under reduced pressure, then partitioned between 50 mL chloroform and 25 mL saturated aqueous sodium carbonate. Concentration of the combined extracts after drying over magnesium sulfate gave 3-aminomethyl-pyrrolidine-1-carboxylic acid benzyl ester:

Workup

  1. customcarefully quenched with 50 mL of 3N HCl
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompartitioned between 50 mL chloroform and 25 mL saturated aqueous sodium carbonate
  4. dry with materialConcentration of the combined extracts after drying over magnesium sulfate

Sources & evidence

ORD record
ord-5349ceea7ed94e5daf2670ab5c393e60
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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