Sodium borohydride → 2-Amino-alpha-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol

HRID 1808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[O:20][CH3:21])=[O:5].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH:4]([OH:5])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[O:20][CH3:21]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 540054462-Amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone

Produkt 1

HCID 539319582-Amino-alpha-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcoholAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone (10 g) in methanol (100 ml) was added sodium borohydride (1.4 g). After being stirred for 24 h, the mixture was concentrated in vacuo. The residue was diluted with water (200 ml) and extracted with ethyl acetate (300 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1) to give 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g) as colorless crystals (mp=101°-103° C.).

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted with water (200 ml)
  3. extractionextracted with ethyl acetate (300 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8a08d4d95931403fb13cf9932fe3b98e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726306

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