HCID 68179174, compound → HCID 67113783, compound

HRID 1507674Notes

Reaction equation

HRID 1507674 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:10][CH2:9][C@@H:8]([C:11]([O:13]CC3C=CC=CC=3)=[O:12])[CH2:7]2)[C:5](=[O:21])[NH:4][C:3]1=[O:22]>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]1[C:6]2([CH2:10][CH2:9][C@@H:8]([C:11]([OH:13])=[O:12])[CH2:7]2)[C:5](=[O:21])[NH:4][C:3]1=[O:22]

Participants

4

Reactant 1

HCID 68179174HCID 68179174, compound

Product 1

HCID 67113783HCID 67113783, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To (7R)-benzyl 1-methyl-2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate (from step A, 0.1 g, 0.331 mmol) in ethyl acetate (10 mL) was added Pd—C (0.035 g, 0.033 mmol) under a nitrogen atmosphere. The contents were hydrogenated at 20 psi for 1 hour. The reaction mixture was filtered over a Whatman filter (FN MB 25 MM 0.45 uM) paper and washed with ethyl acetate (2×5 mL). The filtrate was concentrated under reduced pressure to yield an oil (0.05 g, 0.236 mmol, 71.2%) which was used in the next step without further purification. MS m/z 211.3 (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 ethyl acetate (2×5 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-99de4c10bef14f5987b10b3df0349c99
Source dataset
uspto-grants-2015_12
Patent number
US09221819B2

Reaction notes

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