Diboron → N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

HRID 1587945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587945
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[C:21](=O)[CH2:20][O:19][CH:18]([C:23]3[N:24]=[C:25]([C:28]([F:31])([F:30])[F:29])[S:26][CH:27]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].B#B>O1CCCC1>[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[CH2:21][CH2:20][O:19][CH:18]([C:23]3[N:24]=[C:25]([C:28]([F:29])([F:31])[F:30])[S:26][CH:27]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 6328200DiboronHCID 19974202N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholin-5-one

Produkt 1

HCID 19974360N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1 g (0.0022 Mol) of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholin-5-one (diastereomer A) is dissolved in 6 ml of absolute tetrahydrofuran. At room temperature 15 ml (0.015 Mol) of a one molar solution of diborane in tetrahydrofuran is added dropwise within 15-20 minutes. During this the solution heated up to about 35°-40° C. After 30 minutes the mixture is evaporated to dryness and the remaining residue is dissolved in 40 ml of methanol and 2 ml of concentrated hydrochloric acid, and the mixture is left to stand for 30 minutes. While cooling in ice, the mixture is made alkaline with ammonia and is extracted several times by shaking with methylene chloride. The organic phase is dried over sodium sulphate and the base is purified on a silica gel column using toluene/ethyl acetate=7.5:2.5 as eluant.

Aufarbeitung

  1. temperatureDuring this the solution heated up to about 35°-40° C
  2. customAfter 30 minutes the mixture is evaporated to dryness
  3. dissolutionthe remaining residue is dissolved in 40 ml of methanol
  4. wait2 ml of concentrated hydrochloric acid, and the mixture is left
  5. temperatureWhile cooling in ice
  6. extractionis extracted several times
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customthe base is purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-faa83ed9604e4371800d86ace70d5351
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219852

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