Ammonia → tert-Butyl [(3-aminooxetan-3-yl)methyl]carbamate

HRID 1910440Notes

Reaction equation

HRID 1910440 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][O:11][CH2:10]1)C1C=CC=CC=1.FC(F)(F)C(O)=O.N>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:12][O:11][CH2:10]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 71262160HCID 71262160, compound

Product 1

HCID 71254478tert-Butyl [(3-aminooxetan-3-yl)methyl]carbamateYield 84.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of tert-butyl {[3-(dibenzylamino)oxetan-3-yl]methyl}carbamate (13.0 g, crude), 20% palladium hydroxide on carbon (2.0 g) and trifluoroacetic acid (0.5 mL) in methanol (20 mL) was stirred overnight under hydrogen atmosphere (1 bar). After being basified with ammonia solution in methanol, the resulting mixture was filtered and concentrated in vacuo to afford 5.8 g of the crude product, which was used for the next step without any purification.

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-554ef2a91a3b4d7c8c8fdd6b83323ef9
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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