Acetic Acid → tert-Butyl [(azetidin-2-yl)methyl]carbamate

HRID 868142Notes

Reaction equation

HRID 868142 reaction equation
C([N:8]1[CH2:11][CH2:10][CH:9]1[CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C1C=CC=CC=1.C(O)(=O)C.[H][H]>[Pd].O1CCCC1>[C:17]([O:16][C:14]([NH:13][CH2:12][CH:9]1[CH2:10][CH2:11][NH:8]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14280901HCID 14280901, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14280902tert-Butyl [(azetidin-2-yl)methyl]carbamateYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 18.8 g (68.0 mmol) of 1-benzyl2-[(t-butoxycarbonylamino)methyl]azetidine, 8.2 g (137 mmol) of acetic acid, 1.0 g of 20% palladium on carbon and 200 ml of tetrahydrofuran was shaken in a hydrogen atmosphere at pressures of 48.3-51.7 psi and temperatures of 21.5°-27° for 16 hours. The catalyst was removed by filtration and the solvent was removed. in vacuo to give 11.7 g (92%) of the title compound as a colorless viscous oil which was used without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-db3638581f114a9398391cd5f7e7023d
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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