1-Iodopropane → HCID 57941436, compound

HRID 1437922Notes

Reaction equation

HRID 1437922 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[NH:9]1.I[CH2:23][CH2:24][CH3:25]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[N:9]1[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 336431-IodopropaneHCID 57941332HCID 57941332, compound2×

Product 1

HCID 57941436HCID 57941436, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of a (4S,7R)-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 12; 150 mg, 0.52 mmol) and 1-iodopropane (103 μL, 1.05 mmol) in N,N-dimethylformamide (2 mL) in a microwave reaction tube was heated to 100° C. and stirred for 18 h. The reaction mixture was allowed to cool, diluted with saturated sodium bicarbonate, and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified using an ISCO CombiFlash® Sg100c chromatography system with an Isco 12 g column, eluting with 25-100% ethyl acetate/hexanes to give (4S,7R)-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1-propyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (59.7 mg, 35%) as an orange oil. ES(+)-MS (M+H) 329.

Workup

  1. customin a microwave reaction tube
  2. temperatureto cool
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified
  9. washeluting with 25-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7a41ed7aaad54568b7e508850db6da7a
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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