Sodium Hydroxide → 1-[(R)-tetrahydro-2-furoyl]-4-Boc-piperazine

HRID 500642

Reaktionsgleichung

Reaktionsgleichung von HRID 500642
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([OH:8])=O.S(Cl)(Cl)=O.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([N:23]1[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]1)=[O:8]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2734707Tetrahydro-2-furoic acid, (+)-

Produkt 1

HCID 668793671-[(R)-tetrahydro-2-furoyl]-4-Boc-piperazineAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (R)-tetrahydro-2-furoic acid (5 g, 43.06 mmol) in toluene (75 mL) was added thionyl chloride (7.68 g, 64.6 mmol). The mixture was stirred at 90° C. for 2 h, then slowly cooled to 0° C. To a separate flask was charged a solution of N-Boc piperazine (8.02 g, 43.06 mmol) in toluene (40 mL), and aqueous sodium hydroxide (10.3 g, 258 mmol) in water (80 mL). This biphasic solution was cooled in an ice bath, followed by the addition of the cold acid chloride prepared above. The mixture was stirred vigorously for 2 h. The organic phase was collected, and washed with 1M H3PO4, dried and evaporated, to provide the title intermediate (9.87 g).

Aufarbeitung

  1. temperatureslowly cooled to 0° C
  2. temperatureThis biphasic solution was cooled in an ice bath
  3. customprepared above
  4. stirringThe mixture was stirred vigorously for 2 h
  5. customThe organic phase was collected
  6. washwashed with 1M H3PO4
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fad966eed5e04b9ab4091a799a8640ec
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772239B2

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