HCID 67051804, compound → HCID 55288477, compound

HRID 1809004Notes

Reaction equation

HRID 1809004 reaction equation
C1(COC([N:11]2[CH2:14][C:13]3([C@@H:18]([CH3:19])[NH:17][C:16](=[O:20])[O:15]3)[CH2:12]2)=O)C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:19][C@@H:18]1[C:13]2([CH2:14][NH:11][CH2:12]2)[O:15][C:16](=[O:20])[NH:17]1

Participants

5

Reactant 2

HCID 67051804HCID 67051804, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 55288477HCID 55288477, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (8R)-8-methyl-6-oxo-5-oxa-2,7-diazaspiro[3.4]octane-2-carboxylic acid phenylmethyl ester (1.84 g, 6.6 mmol) in methanol (66 mL) was added wet 10% palladium on carbon (50% by mass, 500 mg). The resulting suspension was stirred under 1 atm of hydrogen for 1 h. The catalyst was then removed by filtration through celite. The filtrate was concentrated in vacuo to provide (8R)-8-methyl-5-oxa-2,7-diazaspiro[3.4]octan-6-one as a white solid (0.99 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 5.23 (br s, 1H), 4.07 (d, 1H), 4.02 (d, 1H), 3.92 (d, 1H), 3.79 (d, 1H), 3.58 (d, 1H), 1.38 (d, 3H); MS (EI) for C6H10N2O2: 143 (MH+).

Workup

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

Sources & evidence

ORD record
ord-f7a347756ae1490f8e857519188fd09a
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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