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

HRID 477133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477133
[OH:1][CH:2]([C:5]1[N:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[S:8][CH:9]=1)[CH2:3][NH2:4].[C:14]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=O)[CH3:28])=[CH:22][CH:21]=1)([O:16][CH3:17])=[O:15].C([BH3-])#N.[Na+]>CO>[C:14]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH:27]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[N:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[S:8][CH:9]=2)[CH3:28])=[CH:24][CH:25]=1)([O:16][CH3:17])=[O:15]

Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetateHCID 140762394-Thiazolemethanol, alpha-(aminomethyl)-2-(trifluoromethyl)-

Produkt 1

HCID 14347763N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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 an approximately 50:50 diastereomer mixture of the base. This is recrystallised from a mixture of ether/ethyl acetate=65:10, and twice more from ethyl acetate. This results in diastereomer A in 98-99% purity.

Aufarbeitung

  1. customfollowed by purification on a silica gel column
  2. customThis results in an approximately 50:50 diastereomer mixture of the base
  3. customThis is recrystallised from a mixture of ether/ethyl acetate=65:10
  4. customThis results in diastereomer A in 98-99% purity

Quellen und Nachweise

ORD-Eintrag
ord-09d028cdb07d40519cf283a953966795
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886814

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