Acetic Acid → HCID 25057601, compound

HRID 494162Notes

Reaction equation

HRID 494162 reaction equation
[CH2:1]([CH:5]1[C:9]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[O:8][C:7](=[O:15])[NH:6]1)[CH2:2][CH2:3][CH3:4].[CH3:16][C:17]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:18]=1[C:19]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O.N>C(Cl)Cl>[CH2:1]([CH:5]1[C:9]2([CH2:14][CH2:13][N:12]([CH:24]3[CH2:25][CH2:26][N:21]([C:19](=[O:20])[C:18]4[C:28]([CH3:32])=[CH:29][CH:30]=[CH:31][C:17]=4[CH3:16])[CH2:22][CH2:23]3)[CH2:11][CH2:10]2)[O:8][C:7](=[O:15])[NH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 5049666Sodium triacetoxyborohydrideHCID 20427870HCID 20427870, compoundHCID 59657483HCID 59657483, compound

Product 1

HCID 25057601HCID 25057601, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-butyl-1-oxa-3,8-diaza-spiro[4.5]decane-2-one (12: R=H; R′=n-Bu; 1.09 g; 5.1 mmol)) in 30 mL DCM was added 1.24 g (5.4 mmol) of 1-(2,6-dimethyl-benzoyl)-piperidin-4-one followed by 2.1 mL (7.1 mmol) of Ti(IV)(O-i-Pr)4 The reaction mixture stirred under nitrogen for 18 h. of Sodium triacetoxyborohydride (1.6 g: 7.7 mmol) was added to the reaction mixture followed by glacial HOAc (0.365 mL; 6.4 mmol). The reaction mixture stirred for 24 h. Aqueous ammonia (20 mL; 10% aqueous solution) was added and the solution stirred for an additional 10 min. The mixture was filtered by gravity through a cartridge of ChemElute™. The organics were evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel with gradient elution (2% to 10% methanol in ethyl acetate with 0.4% ammonia) to provide 1.6 g (73%) of 4-butyl-8-[1-(2,6-dimethyl-benzoyl)-piperidin-4-yl]-1-oxa-3,8-diaza-spiro[4.5]decane-2-one: ms [M]+=428.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe solution stirred for an additional 10 min
  3. filtrationThe mixture was filtered by gravity through a cartridge of ChemElute™
  4. customThe organics were evaporated under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel with gradient elution (2% to 10% methanol in ethyl acetate with 0.4% ammonia)

Sources & evidence

ORD record
ord-30fbf80bd12741bca97030604c9c65bf
Source dataset
uspto-grants-2009_05
Patent number
US07538122B2

Reaction notes

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