Ethyl 6-methoxy-1H-indole-2-carboxylate → Rac-6-methoxy-2,3-dihydro-1h-indole-2-carboxylic acid ethyl ester

HRID 556473

Reaktionsgleichung

Reaktionsgleichung von HRID 556473
C([BH3-])#N.[Na+].[CH2:5]([O:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=2)=[O:9])[CH3:6]>C(O)(C(F)(F)F)=O>[CH2:5]([O:7][C:8]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:19][CH3:20])=[CH:15][CH:16]=2)[NH:11]1)=[O:9])[CH3:6]

Komponenten

4

Edukt 2

HCID 612959Ethyl 6-methoxy-1H-indole-2-carboxylateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 57479057Rac-6-methoxy-2,3-dihydro-1h-indole-2-carboxylic acid ethyl esterAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (750 mg, 12 mmol) (Aldrich) was added in small portions to a mixture of 6-Methoxy-1H-indole-2-carboxylic acid ethyl ester (500 mg, 2.4 mmol) (Aldrich) in TFA (10 mL), which was cooled in ice-water bath, at such a rate that gas evolution was not too vigorous. When the addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hr. The resulting mixture was concentrated in vacuo and the residue was dissolved in DCM. The organic layer was washed with Na2CO3 solution, dried with Na2SO4, and concentrated to give 400 mg rac-6-Methoxy-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester. MS: [M+H]+=222

Aufarbeitung

  1. additionWhen the addition
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. washThe organic layer was washed with Na2CO3 solution
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3b507d3ac117459fb37570dde41f7ff5
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058269B2

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