Sodium Bicarbonate → HCID 22722137, compound

HRID 349174Notes

Reaction equation

HRID 349174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[N:17]4[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:16]4=[N:15][N:14]=3)[CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.[CH3:24][Si]([N-][Si](C)(C)C)(C)C.[K+].C(=O)(O)[O-].[Na+]>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[N:17]4[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:16]4=[N:15][N:14]=3)[CH2:11][C:10](=[CH2:24])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22722121HCID 22722121, compound

Product 1

HCID 22722137HCID 22722137, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Chlorophenyl)-3-(5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)cyclobutanone (4-5) (52 mg) was dissolved in freshly distilled tetrahydrofuran (2 mL). Methyltriphenylphosphonium bromide (281 mg) was added followed by potassium bis(trimethylsilyl)amide (KHMDS, 0.5M in toluene, 1.25 mL). After stirring for 24 hours at room temperature, the crude product was added to a saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated. The product was purified by silica gel column chromatography to give 3-[1-(4-chlorophenyl)-3-methylenecyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (4-6).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was collected
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bfb3936a3ba74d12a626354f5c1db907
Source dataset
uspto-grants-2007_02
Patent number
US07179802B2

Reaction notes

Loading…