Tert-butyl 3-(2-(((benzyloxy)carbonyl)(methyl)amino)acetamido)azetidine-1-carboxylate → Tert-butyl 3-(2-(methylamino)acetamido)azetidine-1-carboxylate

HRID 2175574Notes

Reaction equation

HRID 2175574 reaction equation
C(O[C:9]([N:11](C)[CH2:12][C:13]([NH:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)=[O:14])=O)C1C=CC=CC=1>[Pd]>[CH3:9][NH:11][CH2:12][C:13]([NH:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)=[O:14]

Participants

3

Reactant 1

HCID 58562550Tert-butyl 3-(2-(((benzyloxy)carbonyl)(methyl)amino)acetamido)azetidine-1-carboxylate

Product 1

HCID 18699830Tert-butyl 3-(2-(methylamino)acetamido)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a flask containing tert-butyl 3-(2-(((benzyloxy)carbonyl)(methyl)amino)acetamido)azetidine-1-carboxylate (3.10 g, 8.21 mmol, prepared in the previous step) and a stirbar, was added 10% Pd/C (136 g, 0.127 mmol). The flask was evacuated and back filled with argon. Methanol (100 mL) was carefully added via syringe and the flask was evacuated with stirring. It was then back filled with hydrogen and stirred 2 days under a hydrogen balloon. After evacuation with stirring and back filling with argon, the catalyst was removed by filtration over Celite 521 and concentrated in vacuo to afford the product.

Workup

  1. customprepared in the previous step) and a stirbar
  2. customThe flask was evacuated
  3. additionback filled with argon
  4. additionMethanol (100 mL) was carefully added via syringe
  5. customthe flask was evacuated
  6. additionIt was then back filled with hydrogen
  7. stirringstirred 2 days under a hydrogen balloon
  8. stirringAfter evacuation with stirring
  9. customthe catalyst was removed by filtration over Celite 521
  10. concentrationconcentrated in vacuo
  11. customto afford the product

Sources & evidence

ORD record
ord-38d08e6b647945349d50ce0689c2cb7f
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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