HCID 131726882, compound → HCID 131726881, compound

HRID 2223334Notes

Reaction equation

HRID 2223334 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:14]1[CH2:31][C@@:29]2([CH3:30])[C@@H:25]([CH2:26][CH2:27][C@@H:28]2[O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C@@:24]2([C:39]#[N:40])[C:15]=1[C:16]1[CH:17]=[CH:18][C:19]([O:41][CH3:42])=[CH:20][C:21]=1[CH2:22][CH2:23]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.CO.[Pd]>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH2:31][C@@:29]2([CH3:30])[C@@H:25]([CH2:26][CH2:27][C@@H:28]2[O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C@@:24]2([C:39]#[N:40])[C:15]=1[C:16]1[CH:17]=[CH:18][C:19]([O:41][CH3:42])=[CH:20][C:21]=1[CH2:22][CH2:23]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 131726882HCID 131726882, compound

Product 1

HCID 131726881HCID 131726881, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 15.26 g of alkyne 3 in 300 ml of tetrahydrofuran/methanol (3:1) is mixed with 2.7 g of palladium (10% on magnesium carbonate) and stirred at room temperature under a hydrogen atmosphere (1 bar) until the reaction is completed. For working-up, it is filtered on Celite and concentrated by evaporation in a vacuum. 15.4 g of a colorless foam 4 is obtained, which is used without further purification in the next stage (GC-MS: m/z theor.: 569, pract.: 569).

Workup

  1. filtrationit is filtered on Celite
  2. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-67ccef44194a4cfba575df18b56e7fb7
Source dataset
uspto-grants-2008_05
Patent number
US07375098B2

Reaction notes

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