alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide → (S)-2-Amino-5-(3-pyridyl)pentane

HRID 2073303Notes

Reaction equation

HRID 2073303 reaction equation
OC(C1C=CC=CC=1)C([NH:5][CH:6]([CH3:16])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O>Cl>[CH3:16][C@H:6]([NH2:5])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 13999762alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide

Product 1

HCID 13739742(S)-2-Amino-5-(3-pyridyl)pentane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of 160 g of crude [S-(R*,R*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide in 800 mL of 6N HCl was treated with 85 mL conc. HCl and then was heated at reflux overnight as described in Example 16. The crude amine (~85 g), isolated in the normal manner was distilled to furnish 76.4 g of (S)-alpha-methyl-3-pyridinebutanamine, (60% ee; bp 89°-91°/0.15 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe crude amine (~85 g), isolated in the normal manner
  4. distillationwas distilled

Sources & evidence

ORD record
ord-9f6517f5f2b34d7887e8fe0b10523286
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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