1,1-dimethylethyl{(1R)-1-[3-hydroxy-1-(phenylmethyl)azetidin-3-yl]ethyl}carbamate → HCID 86621270, compound

HRID 605746Notes

Reaction equation

HRID 605746 reaction equation
CC([N:5]([C@@H:9]([C:11]1([OH:22])[CH2:14][N:13](CC2C=CC=CC=2)[CH2:12]1)[CH3:10])[C:6](=[O:8])[O-:7])(C)C.[H][H]>CO.[Pd]>[OH:22][C:11]1([C@H:9]([NH:5][C:6](=[O:8])[O:7][C:11]([CH3:14])([CH3:12])[CH3:9])[CH3:10])[CH2:12][NH:13][CH2:14]1

Participants

5

Reactant 2

HCID 867612951,1-dimethylethyl{(1R)-1-[3-hydroxy-1-(phenylmethyl)azetidin-3-yl]ethyl}carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86621270HCID 86621270, compoundYield 211.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl{(1R)-1-[3-hydroxy-1-(phenylmethyl)azetidin-3-yl]ethyl}carbamate (1.07 g, 3.5 mmol) in methanol was added wet 10% palladium on carbon (50% by mass, 250 mg). The resulting suspension was subjected to 1 atmosphere of hydrogen for 7 h, and an additional 250 mg of catalyst was added over the course of the reaction. The catalyst was then removed by filtration through celite. The filtrate was then concentrated in vacuo to provide 1,1-dimethylethyl [(1R)-1-(3-hydroxyazetidin-3-yl)ethyl]carbamate as a colorless syrup (800 mg, quantitative yield). MS (EI) for C10H20N2O3: 161 (M-tert-butyl+H).

Workup

  1. customThe catalyst was then removed by filtration through celite
  2. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-e3d3b7d6ba744fc3810430df5aef2814
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

Loading…