(7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate → (7R)-2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylic acid

HRID 1507673Notes

Reaction equation

HRID 1507673 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:11][CH2:10][C@@H:9]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])[CH2:8]2)[NH:3]1>CO.[Pd]>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:11][CH2:10][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:8]2)[NH:3]1

Participants

4

Reactant 1

HCID 68179167(7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

Product 1

HCID 67113813(7R)-2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To (7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate (from step A, 0.14 g, 0.486 mmol) in methanol (10 mL) was added Pd—C (0.030 g, 0.282 mmol) under a nitrogen atmosphere. The contents were hydrogenated at 10 psi for 3 hours. The reaction mixture was filtered over a whatman filter (FN MB 25 MM 0.45 uM) paper and washed with methanol (2×5 mL). The filtrate was concentrated under reduced pressure to yield a solid (0.09 g, 0.454 mmol, 94% yield). It was used as such for the subsequent step without further purification. MS m/z 197.3 (M−H)+

Workup

  1. filtrationThe reaction mixture was filtered over a whatman
  2. filtrationfilter (FN MB 25 MM 0.45 uM) paper
  3. washwashed with methanol (2×5 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-77857247de244f0091d3678132573948
Source dataset
uspto-grants-2015_12
Patent number
US09221819B2

Reaction notes

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