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

HRID 1672945Notes

Reaction equation

HRID 1672945 reaction equation
[OH:1][C:2]1([C@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH2:5][N:4](CC2C=CC=CC=2)[CH2:3]1.[H][H]>CO.[Pd]>[OH:1][C:2]1([C@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH2:3][NH:4][CH2:5]1

Participants

5

Reactant 2

HCID 866212691,1-dimethylethyl {(1R)-1-[3-hydroxy-1-(phenylmethyl)azetidin-3-yl]ethyl}carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86621270HCID 86621270, compoundYield 105.7%

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-36ba30af452c4afe9e5a1b398fe73959
Source dataset
uspto-grants-2011_08
Patent number
US07999006B2

Reaction notes

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