Isopropyl chloroformate → (3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Isopropyl Ester Hydrochloride

HRID 1182172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182172
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][NH:21][CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:5][CH:4]=1.[CH:33]([O:36][C:37]([Cl:39])=[O:38])([CH3:35])[CH3:34].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:39].[CH:33]([O:36][C:37]([N:21]1[CH2:22][C@H:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:19]([CH2:18][N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:30])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:32][CH:31]=4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH2:20]1)=[O:38])([CH3:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 114646642-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

Produkt 1

HCID 67368814(3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Isopropyl Ester HydrochlorideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one (60 μmol) in anhydrous DCM (1 mL) was added isopropylchloroformate (180 μL, 1M in toluene, 180 μmol) and triethylamine (29 μL, 55 μmol). The reaction mixture was stirred overnight at room temperature. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture and the aqueous layer washed with dichloromethane (3×2 mL). The organic layer was then concentrated in vacuo and purified by semi-preparative HPLC (Method D) and lyophilized to give the Compound 183 as a colorless solid (15.3 mg, 50%).

Aufarbeitung

  1. washthe aqueous layer washed with dichloromethane (3×2 mL)
  2. concentrationThe organic layer was then concentrated in vacuo
  3. custompurified by semi-preparative HPLC (Method D)

Quellen und Nachweise

ORD-Eintrag
ord-b70cd91e2a464b3f99dfe0e0782d4201
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288548B2

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