Benzyl 3-(azidomethyl)cyclobutanecarboxylate → 3-(Aminomethyl)cyclobutanecarboxylic acid

HRID 1969576Notes

Reaction equation

HRID 1969576 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:8][CH:7]([C:9]([O:11]CC2C=CC=CC=2)=[O:10])[CH2:6]1)=[N+]=[N-]>[Pd].CO>[NH2:1][CH2:4][CH:5]1[CH2:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6]1

Participants

4

Reactant 1

HCID 86660436Benzyl 3-(azidomethyl)cyclobutanecarboxylate

Product 1

HCID 585579013-(Aminomethyl)cyclobutanecarboxylic acidYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask charged with 10% palladium on carbon (0.20 g, 0.19 mmol) was added a solution of benzyl 3-(azidomethyl)cyclobutanecarboxylate (2.00 g, 8.15 mmol, prepared using IIII from benzyl 3-(hydroxymethyl)cyclobutanecarboxylate (Parkway Scientific), JJJJ with sodium azide) in MeOH (100 mL). The reaction mixture was sparged with hydrogen and an atmosphere of hydrogen was maintained via a balloon. The reaction mixture was stirred for about 4 h at ambient temperature and then was filtered through a pad of Celite®, washed with MeOH and concentrated in vacuo to give the crude 3-(aminomethyl)cyclobutanecarboxylic acid (1.08 g, 100%) which was used without further purification: LC/MS (Table 1, Method r) Rt=2.41 min (ELSD); MS m/z: 130 (M+H)+.

Workup

  1. customThe reaction mixture was sparged with hydrogen
  2. temperaturean atmosphere of hydrogen was maintained via a balloon
  3. filtrationwas filtered through a pad of Celite®
  4. washwashed with MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b7c3b3abd3a4d9eb3793ae880d10f5a
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…