HCID 86668859, compound → HCID 67113836, compound

HRID 331091Notes

Reaction equation

HRID 331091 reaction equation
[O:1]=[C:2]1[NH:21][CH2:20][CH2:19][C:4]2([CH2:8][C@H:7]([C:9]([O:11]CC3C=CC=CC=3)=[O:10])[CH2:6][CH2:5]2)[NH:3]1>CO.[Pd]>[O:1]=[C:2]1[NH:21][CH2:20][CH2:19][C:4]2([CH2:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][CH2:5]2)[NH:3]1

Participants

4

Reactant 1

HCID 86668859HCID 86668859, compound

Product 1

HCID 67113836HCID 67113836, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R)-benzyl 7-oxo-6,8-diazaspiro[4.5]decane-2-carboxylate (from step E, 20 mg, 0.069 mmol) in methanol (2 mL) was added palladium (Pd/C, 10% wt., 7.38 mg, 6.94 μmol). The resulting mixture was stirred under a hydrogen balloon for 30 min. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure to yield (2R)-7-oxo-6,8-diazaspiro[4.5]decane-2-carboxylic acid (10 mg, 0.050 mmol, 72.7% yield) as an oil. It was used as such for the next step without further purification. MS m/z 199 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e46f0ef5411498f85d8ba5ee1249b79
Source dataset
uspto-grants-2014_11
Patent number
US08877749B2

Reaction notes

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