2-[(2S)-2-[[(2R)-2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide → 2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

HRID 1003287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003287
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:35])[CH2:16][NH:17][C@H:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][C:22]([O:28][CH2:29][C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:23][CH:24]=3)[CH2:19]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:35][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[CH2:16][NH:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][C:30]([N:32]([CH3:33])[CH3:34])=[O:31])=[CH:23][CH:24]=2)[CH2:19]1

Komponenten

4

Edukt 1

HCID 573186072-[(2S)-2-[[(2R)-2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

Produkt 1

HCID 98214472-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamideAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-[(2S)-2-[[(2R)-2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (273 mg) and 10% palladium on activated carbon (60 mg) were suspended in ethanol (5.5 ml). After the mixture was stirred at room temperature for 12 hours under hydrogen atmosphere, the catalyst was filtered off and the filtrate was concentrated in vacuo. Recrystallization of the resulting residue from methanol gave 2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (200 mg) having a melting point of 169-172° C.

Aufarbeitung

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customRecrystallization of the resulting residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-9c31e155e3f2447fabb1c068d27f5689
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046192

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