1-(1H-Pyrazol-1-yl)ethanone → HCID 117697480, compound

HRID 1778477Notes

Reaction equation

HRID 1778477 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][C:15](=[O:17])[CH2:16][CH:9]1[CH2:10][O:11][CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.N1([C:33](=[O:35])[CH3:34])C=CC=N1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH:14]([C:33](=[O:35])[CH3:34])[C:15](=[O:17])[CH2:16][CH:9]1[CH2:10][O:11][CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5492781-(1H-Pyrazol-1-yl)ethanoneHCID 2733832Lithium HexamethyldisilazideHCID 185070529-Boc-7-oxa-9-azabicyclo[3.3.1]nonan-3-one

Product 1

HCID 117697480HCID 117697480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (482 mg, 2 mmol) in THF (5 mL) was added LiHMDS (3 mL, 3 mmol) slowly at −78° C. After 15 mins, 1-pyrazol-1-yl-ethanone (264 mg, 2.4 mmol) was added, and the resulting mixture was stirred at −78° C. for 1 hour and then at room temperature for 1 hour. The reaction mixture was quenched with water, and then extracted with EA (20 mL×2). The organic layer was concentrated in vacuo. The residue was purified by flash chromatography (EA in PE 0%˜70%) to afford 6-acetyl-7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (compound AL) as light yellow oil (56 mg, 20%). LC/MS: calc'd 284 (MH+), exp 284 (MH+).

Workup

  1. waitat room temperature for 1 hour
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EA (20 mL×2)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe residue was purified by flash chromatography (EA in PE 0%˜70%)

Sources & evidence

ORD record
ord-0d0ab5e5221e447793f1df53e3710fda
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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