Triphenylphosphine → tert-Butyl 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate

HRID 1820245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820245
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:21])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[C:4]([CH2:22]O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8]1([CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:12][CH2:13]1)[O:21][CH2:22]2

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57889172tert-Butyl 4-(4-chloro-2-(hydroxymethyl)phenyl)-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 57889918tert-Butyl 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-(4-chloro-2-(hydroxymethyl)phenyl)-4-hydroxypiperidine-1-carboxylate (1.3 g, 3.80 mmol) and triphenylphosphine (1.496 g, 5.70 mmol) in THF (20 mL) was treated with DEAD (0.903 mL, 5.70 mmol), and the mixture was stirred overnight at room temperature. The mixture was concentrated in-vacuo, and the residue was purified over silica gel, eluting with ethyl acetate/hexanes (5%-25% ethyl acetate), to yield the title compound (1.19 g, 3.67 mmol, 97% yield) as a colorless oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated in-vacuo
  2. customthe residue was purified over silica gel
  3. washeluting with ethyl acetate/hexanes (5%-25% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d4bd90ccc25a4e43a4be793b1d2b00c5
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601844B2

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