5-(4-Fluorophenyl)pyridine-3-carbaldehyde → Sarizotan

HRID 1825292Notes

Reaction equation

HRID 1825292 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4]1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]([CH:26]=O)[CH:23]=[N:24][CH:25]=2)=[CH:16][CH:15]=1.[H][H]>C1COCC1.[Pd]>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[C:22]([CH2:26][NH:1][CH2:2][C@H:3]3[CH2:12][CH2:11][C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[O:4]3)[CH:23]=[N:24][CH:25]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 98776715-(4-Fluorophenyl)pyridine-3-carbaldehydeHCID 10203113(R)-chroman-2-ylmethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 6918388SarizotanYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.07 g of (R)-2-aminomethylchroman and 5.00 g of 5-(4-fluorophenyl)-pyridine-3-carbaldehyde are dissolved in 38 ml of THF, and 6 g of 5% palladium on activated carbon are added with stirring. The mixture is hydrogenated at room temperature under atmospheric pressure with stirring. When the take-up of hydrogen is complete, the catalyst is filtered off, giving 8.66 g of (R)-(−)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]chroman by removal of the solvent by distillation (68% yield).

Workup

  1. customis hydrogenated at room temperature under atmospheric pressure
  2. stirringwith stirring
  3. filtrationthe catalyst is filtered off

Sources & evidence

ORD record
ord-36e9814586784b68884e9e6e3a4d730a
Source dataset
uspto-grants-2006_05
Patent number
US07045629B2

Reaction notes

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