Acetyl chloride → tert-Butyl (1-acetylazetidin-3-yl)(methyl)carbamate

HRID 17423Notes

Reaction equation

HRID 17423 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15]1)(C1C=CC=CC=1)[C:2]1C=CC=CC=1.C(N(CC)CC)C.C(Cl)(=[O:36])C>[OH-].[Pd+2].[OH-].[C].CO>[C:1]([N:14]1[CH2:17][CH:16]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15]1)(=[O:36])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 53446336tert-Butyl (1-benzhydrylazetidin-3-yl)(methyl)carbamate

Product 1

HCID 86630849tert-Butyl (1-acetylazetidin-3-yl)(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl N-(1-benzhydrylazetidin-3-yl)-N-methylcarbamate (I-149) (0.40 g, 1.13 mmol) was dissolved methanol (20 ml), then 20% palladium hydroxide-carbon (containing about 50% water, 20 g) was added, followed by stirring at room temperature under hydrogen atmosphere for 15 hours, and the catalyst was removed by filtration. The solvent was evaporated away under reduced pressure, the resulting residue was dissolved in dichloromethane (10 ml), and triethylamine (0.20 ml, 3.44 mmol) and acetyl chloride (90.0 μl, 26 mmol) were added.

Workup

  1. customthe catalyst was removed by filtration
  2. customThe solvent was evaporated away under reduced pressure
  3. dissolutionthe resulting residue was dissolved in dichloromethane (10 ml)

Sources & evidence

ORD record
ord-6d08f09e04354710a17d0a32a3d6a5cd
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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