Ethanol → HCID 9847522, compound

HRID 843576Notes

Reaction equation

HRID 843576 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:22][CH:21]=1)=[O:19])[C:13]([C:35]1[CH:40]=[CH:39][C:38]([O:41]CC3C=CC=CC=3)=[CH:37][CH:36]=1)=[C:12]2[CH3:49])C1C=CC=CC=1.C(O)C.C1CCC=CC=1>C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:24][CH:25]=1)=[O:19])[C:13]([C:35]1[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=1)=[C:12]2[CH3:49]

Participants

6

Reactant 3

HCID 702EthanolHCID 116051,3-CyclohexadieneHCID 9939438HCID 9939438, compound

Product 1

HCID 9847522HCID 9847522, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.78 g (0.00120 mol) of [5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-indol-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (described above) in 5 mL of dry THF, and 5 mL of punctilious ethanol, under N2, was added 1.4 mL (0.0120 mol) of cyclohexadiene and 0.39 g (one-half the mass of the benzyloxy starting material) of 10% Pd/C, and stirred at room temperature overnight. The reaction mixture was filtered and evaporated to dryness in a rotary evaporator. 100 mL of ethyl acetate was added to the crude product. This organic phase was washed with water (2×50 mL), saturated brine, removed, dried over magnesium sulfate, filtered and evaporated to dryness in a rotary evaporator. The crude product when subjected to HPLC gave 0.30 g of pale-yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness in a rotary evaporator
  3. addition100 mL of ethyl acetate was added to the crude product
  4. washThis organic phase was washed with water (2×50 mL), saturated brine
  5. customremoved
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in a rotary evaporator

Sources & evidence

ORD record
ord-3d959c9b67fe46938b275a10c64b8d5d
Source dataset
uspto-grants-2002_04
Patent number
US06380185B1

Reaction notes

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