Reaktion #564314

Reaktionsgleichung

hydrochloric acid

2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

1-(4-carbomethoxymethoxyphenyl)propan-2-one

sodium cyanoborohydride

→

oil

Ausbeute 92.0%

N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Ausbeute 92.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification on a silica gel column
2. 2
   SonstigeThis results in a 50:50 diastereomer mixture of the base
3. 3
   SonstigeThis is recrystallised from a mixture of ether/ethyl acetate=65:10
4. 4
   SonstigeThe mother liquor resulting from
5. 5
   Sonstigethe mixture is evaporated to dryness
6. 6
   SonstigeThe residue resulting from
7. 7
   Sonstigethis is recrystallised from a mixture of ether/ethyl acetate/methanol=100:60:1
8. 8
   Sonstigehave been removed by filtration
9. 9
   Sonstigeis evaporated to dryness
10. 10
    Sonstigepurified on a silica gel column

Vorschrift

Prepared by analogy to Example 13 by reaction of 2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine with 1-(4-carbomethoxymethoxyphenyl)propan-2-one and sodium cyanoborohydride in methanol (reaction time: 5 hours) followed by purification on a silica gel column using methylene chloride/methanol=20:1. This results in a 50:50 diastereomer mixture of the base. This is recrystallised from a mixture of ether/ethyl acetate=65:10. The mother liquor resulting from this is mixed with ethereal hydrochloric acid, and the mixture is evaporated to dryness. The residue resulting from this is recrystallised from a mixture of ether/ethyl acetate/methanol=100:60:1. The mother liquor obtar,ned after the crystals have been removed by filtration is evaporated to dryness, and the base is liberated by shaking with alkali and methylene chloride and purified on a silica gel column using methylene chloride/methanol=20:1 as eluant. This results in diastereomer B as an oil approximately 92-94% pure.

Quelle