Water → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol

HRID 602756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602756
C[O:2][C:3](=O)[C:4]([S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([CH2:20][O:21][CH3:22])[C:8]=2[CH2:7]1)[CH3:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[C:26]1([S:23]([C:4]([CH:6]2[CH2:18][CH2:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=4)[N:9]([CH2:20][O:21][CH3:22])[C:8]=3[CH2:7]2)([CH3:5])[CH2:3][OH:2])(=[O:25])=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67267086(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester

Produkt 1

HCID 67266793(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 402 mg (0.84 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester in 6 mL of THF, 1.0 mL (1.0 mmol, 1.2 eq) of LiAlH4 in THF was added at RT. After 30 min, the reaction mixture was poured into water and extracted with EtOAc, dried over Na2SO4, and evaporation of the solvent afforded (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol as a colorless oil, MS: 465 (MNH4+). The crude material was used in the next step without further purification.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4, and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-21d2237a432a47d6a46662c8a2949239
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906546B2

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