Acetic Acid → HCID 22055662, compound

HRID 1988989Notes

Reaction equation

HRID 1988989 reaction equation
[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][NH:4][C:3](=[O:12])[CH2:2]1.[CH3:13][C:14]([CH3:16])=O.[BH3-]C#N.[Na+].C(O)(=O)C.C([O-])(O)=O.[Na+]>CO>[CH:14]([N:9]1[CH2:8][CH2:7][C:6]2([O:1][CH2:2][C:3](=[O:12])[NH:4][CH2:5]2)[CH2:11][CH2:10]1)([CH3:16])[CH3:13]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 130594341-Oxa-4,9-diazaspiro(5.5)undecan-3-one

Product 1

HCID 22055662HCID 22055662, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1-Oxa-4,9-diaza-spiro[5.5]undecan-3-one was dissolved in MeOH and treated with acetone (6 equivalents) and NaCNBH3 (4 equivalents). To the reaction mixture was added acetic acid (3 equivalents). The reaction was heated at 50° C. for 6 hours and then cooled to room temperature. The reaction was then poured into an aqueous NaHCO3 solution and extracted with EtOAc (3×). The fractions were dried over MgSO4 and concentrated to provide the title compound as a yellow oil that was purified by chromatography (10% MeOH/CH2Cl2). LC/MS (m/z) 213.1 (MH+), Rt=1.38 minutes.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe fractions were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2ddc75e85fe8439a903eaea6aad1c761
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

Loading…