Iodine → Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[C:9](=O)[NH:8][C:5]2=[CH:6][CH:7]=1.[BH4-].[Na+].II>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of tert-butyl 5-chloro-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.530 g, 1.64 mmol) in UV (5 mL) was added NaBH4 (0.311 g, 8.21 mmol). The reaction was cooled to about −20° C. to −10° C. A solution I2 (0.833 g, 3.28 mmol) in THF (3 mL) was added to the mixture dropwise. The reaction was stirred with warming to about room temperature overnight. The reaction was cooled to about 0° C. and quenched by the addition of saturated NH4Cl, and diluted with DCM. The organics were washed with Na2SO3 and brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by column chromatography to yield tert-butyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.515 g, 100%). LCMS (APCI+) m/z 209, 211 [M+H−Boc]+; Rt=3.67 min.
Aufarbeitung
- temperatureThe reaction was cooled to about −20° C. to −10° C
- temperaturewith warming to about room temperature overnight
- customquenched by the addition of saturated NH4Cl
- additiondiluted with DCM
- washThe organics were washed with Na2SO3 and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-66e7851b7dc34cc3a8aeb81fbf85c2b1
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09346805B2
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