Heptane → HCID 9824113, compound

HRID 1861693Notes

Reaction equation

HRID 1861693 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][OH:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][N:2]=1.C(P(CCCC)CCCC)CCC.[CH3:30][O:31][C:32](=[O:46])[CH:33]([CH2:38][C:39]1[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=1)[C:34]([O:36][CH3:37])=[O:35].CCCCCCC>C1C=CC=CC=1>[CH3:37][O:36][C:34](=[O:35])[CH:33]([CH2:38][C:39]1[CH:40]=[CH:41][C:42]([O:16][CH2:15][CH2:14][N:12]2[C:13]3[CH:1]=[N:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:43][CH:44]=1)[C:32]([O:31][CH3:30])=[O:46]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 13831TributylphosphineHCID 186212892-(9H-beta-Carbolin-9-yl)ethan-1-olHCID 54350942HCID 54350942, compound

Product 1

HCID 9824113HCID 9824113, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 2-β-carbolin-9-yl-ethanol (212 mg, 1.0 mmol), tributylphosphine (303 mg, 1.5 mmol) and 2-(4-hydroxy-benzyl)-malonic acid dimethyl ester (238 mg, 1.0 mmol) were successively dissolved in dry benzene (40 mL). Solid azodicarboxylic dipiperidide (ADDP) (378 mg, 1.5 mmol) was added under stirring at 0° C. to the solution. After 10 min, the reaction mixture was brought to room temperature and the stirring was continued for 16 h. Heptane (10 mL) was added to the reaction mixture and dihydro-ADDP separated out was filtered off. After evaporation of the solvent the product was chromatographed eluting with dichloromethane graduated with ethyl acetate to give 355 mg (82%) of the title compound; 1H NMR (300 MHz, CDCl3): δ 3.10 (d, 2H), 3.55 (t, 1H), 3.65 (s, 6H), 4.35 (t, 2H), 4.75 (t, 2H), 6.70 (d, 2H), 7.05 (d, 2H), 7.30 (t, 1H), 7.3-7.63 (m, 2H), 7.97 (d, 1H), 8.13 (d, 1H), 8.48 (d, 1H), 9.02 (s,1H).

Workup

  1. customwas brought to room temperature
  2. waitthe stirring was continued for 16 h
  3. customseparated out
  4. filtrationwas filtered off
  5. customAfter evaporation of the solvent the product
  6. customwas chromatographed
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c7e085528b624bf59ba3f654365dd3bc
Source dataset
uspto-grants-2003_03
Patent number
US06534517B2

Reaction notes

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