1,1'-Carbonyldiimidazole → HCID 86730133, compound

HRID 1850101Notes

Reaction equation

HRID 1850101 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][CH:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15]1([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C1COCC1.C([O-])(O)=O.[Na+].C(Cl)Cl>[C:22]1([CH:14]2[C:15]3([CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[O:21][C:6](=[O:7])[NH:13]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86730132HCID 86730132, compound

Product 1

HCID 86730133HCID 86730133, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of CDI (388 mg, 2.394 mmol) in THF (1.5 mL) was added slowly a solution of 4-(amino(phenyl)methyl)tetrahydro-2H-pyran-4-ol (451 mg, 2.176 mmol) in THF (3 mL). The mixture was stirred under argon for ˜5 hours. The mixture was diluted with saturated aqueous NaHCO3 solution and DCM. The separated aqueous layer was extracted with DCM (2×) and the combined organic layers were washed with 0.5N aqueous HCl solution and brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 12 g, 0-100% heptane/ethyl acetate] providing 4-phenyl-1,8-dioxa-3-azaspiro[4.5]decan-2-one as a white solid. Yield: 330 mg. LCMS m/z 234.1 (M+H)+; Rt 0.52 min.

Workup

  1. extractionThe separated aqueous layer was extracted with DCM (2×)
  2. washthe combined organic layers were washed with 0.5N aqueous HCl solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography [SiO2, 12 g, 0-100% heptane/ethyl acetate]

Sources & evidence

ORD record
ord-b5249e861a654cc79a91b01d124333ba
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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