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Methanol → 5-Chloro-alpha-(3-tert-butoxycarbonylaminophenyl)-2-neopentylaminobenzyl alcohol

HRID 275848
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 275848
CO.[NH2:3][C:4]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:5]=1[CH:6]([OH:21])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=1.[CH3:27][C:28]([CH3:32])([CH3:31])[CH:29]=O.C([BH3-])#N.[Na+]>C(OC(=O)C)C.C(O)(=O)C>[Cl:26][C:23]1[CH:24]=[CH:25][C:4]([NH:3][CH2:27][C:28]([CH3:32])([CH3:31])[CH3:29])=[C:5]([CH:22]=1)[CH:6]([OH:21])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 540518662-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminophenyl)benzyl alcohol

Produkt 1

HCID 538324135-Chloro-alpha-(3-tert-butoxycarbonylaminophenyl)-2-neopentylaminobenzyl alcoholAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a methanol (4 ml) solution of 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminophenyl) benzyl alcohol (0.4 g) were added trimethyl acetaldehyde (109 mg) and acetic acid (76 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano borohydride (79 mg). The mixture was stirred for one hour at room temperature, to which was added acetic acid ethyl ester (50 ml). The mixture was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography to give the object 5-chloro-α-(3-tert-butoxycarbonylaminophenyl)-2-neopentylaminobenzyl alcohol (0.43 g) as a colorless amorphous solid product.

Aufarbeitung

  1. stirringThe mixture was stirred for one hour at room temperature, to which
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. distillationThe solvent was then distilled off
  5. customthe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c87609a865e3424f8211c7f6361e52b1
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06352982B1

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