Sodium Hydroxide → HCID 12709723, compound

HRID 1018628Notes

Reaction equation

HRID 1018628 reaction equation
[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[NH:14][CH:13](O)[CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[NH:14][CH:13]=[C:12]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12709721HCID 12709721, compound

Product 1

HCID 12709723HCID 12709723, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The intermediate 8-benzyl-3-hydroxy-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one (8.0 g, 23.8 mmol) was dissolved in glacial acetic acid (50 mL) and refluxed for 1.5 h. The reaction mixture was poured into ice water (500 mL) and adjusted to pH 8-9 by. addition of solid sodium hydroxide. The mixture was extracted three times with ethyl acetate (300 mL each). Organic phases were pooled, dried with magnesium sulfate and evaporated. The crude product was recrystallized from methylene chloride to give 8-benzyl-4-phenyl-2,8-diaza-spiro[4.5]dec-3-en-1-one as white crystalls (2.64 g, 35%).

Workup

  1. temperaturerefluxed for 1.5 h
  2. extractionThe mixture was extracted three times with ethyl acetate (300 mL each)
  3. dry with materialdried with magnesium sulfate
  4. customevaporated
  5. customThe crude product was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-122a90304c2f46768bbc696b921d113e
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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