Triethylamine → HCID 10956802, compound

HRID 324623Notes

Reaction equation

HRID 324623 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:12][CH2:13][OH:14])[C:10]=1[OH:11])[C@H:7]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH2:6][CH2:5]2.C(N(CC)CC)C>[C].[Pd].CO>[OH:11][C:10]1[C:9]([CH2:12][CH2:13][OH:14])=[C:8]2[C:4]([CH2:5][CH2:6][C@H:7]2[CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 11068249HCID 11068249, compound

Product 1

HCID 10956802HCID 10956802, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A methanol suspension of (S)-N-[2-(5-bromo-6-hydroxy-7-(2-hydroxyethyl)indan-1-yl)ethyl]propionamide (590 mg, 1.66 mmol.), triethylamine (184 mg, 1.82 mmol.) and 5% palladium-carbon (100 mg) was subjected to catalytic reduction under hydrogen atmosphere. At the time when the calculated volume of hydrogen was absorbed, the catalyst was filtered off. The filtrate was made weakly acidic with dilute hydrochloric acid, followed by extracting the organic matter with a mixture of ethyl acetate:butanol=1.1. The extract solution was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure, followed by washing with diethyl ether to afford the title compound (yield 0.42 g, 91%).

Workup

  1. customAt the time when the calculated volume of hydrogen was absorbed
  2. filtrationthe catalyst was filtered off
  3. extractionby extracting the organic matter
  4. additionwith a mixture of ethyl acetate
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washby washing with diethyl ether

Sources & evidence

ORD record
ord-7e039f65aa3d4d8586ab3dd8ac903b41
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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