Triphenylphosphine → (S)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate

HRID 77028

Reaktionsgleichung

Reaktionsgleichung von HRID 77028
[C:1]1([CH:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OCC)=O)=N\C(OCC)=O>C1COCC1>[C:1]1([CH:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([O:10][C@H:20]2[CH:21]3[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]3)[CH2:19]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 19375alpha-(Phenylamino)benzeneacetic acidHCID 914043-Quinuclidinol, (-)-HCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 59401267(S)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetateAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-phenyl-2-(phenylamino)acetic acid (I1) (500 mg, 2.20 mmol), (R)-quinuclidin-3-ol (280 mg, 2.20 mmol) and triphenylphosphine (577 mg, 2.20 mmol) in dry THF (7 mL) cooled at 0° C., is added (E)-diethyl diazene-1,2-dicarboxylate (0.35 mL, 2.20 mmol) and the reaction is stirred for 2 hours at RT. The solvent is removed under vacuum and the residue is taken up with EtOAc, washed with 5% NaHCO3 and brine, dried over Na2SO4 and evaporated to dryness. The resulting yellow oil is purified by flash chromatography (EtOAc/MeOH/NH4OH=90/10/0.1 to 70/30/0.1) to obtain desired product as a white powder (78.0 mg, 10% yield, mixture of diasteroisomer).

Aufarbeitung

  1. customThe solvent is removed under vacuum
  2. washwashed with 5% NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe resulting yellow oil is purified by flash chromatography (EtOAc/MeOH/NH4OH=90/10/0.1 to 70/30/0.1)

Quellen und Nachweise

ORD-Eintrag
ord-dd71191b9d214878ab797f1eb70b1754
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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