4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester → 4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-[1,4]diazepan-5-one

HRID 2095514Notes

Reaction equation

HRID 2095514 reaction equation
C(OC([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH2:21][C:22]([N:24]2[CH2:31][CH2:30][C:27]3([CH2:29][CH2:28]3)[C@H:26]([OH:32])[CH2:25]2)=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:32][C@@H:26]1[CH2:25][N:24]([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][N:14]2[C:15](=[O:18])[CH2:16][CH2:17][NH:11][CH2:12][CH2:13]2)[CH2:31][CH2:30][C:27]21[CH2:29][CH2:28]2

Participants

5

Reactant 2

HCID 670743214-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 670740504-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-[1,4]diazepan-5-oneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.44 g (1 mmol) of 4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester in 10 ml of MeOH was added 0.05 g of 10% palladium on charcoal. The mixture was stirred under 1 atmosphere of hydrogen for 1.5 h after which time the reaction was filtered through Hyflo and concentrated, affording the titled compound in 85% yield as a colorless foam. MS: 310.4 (MH+).

Workup

  1. filtrationwas filtered through Hyflo
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-977e90cc308d404c91d27f0ebaca3d9d
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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