Sodium borohydride → Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 519330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519330
[C:1]([CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:2].[BH4-].[Na+]>C(O)C>[NH2:2][CH2:1][CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86683734Ethyl 1-(Cyanomethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Produkt 1

HCID 86683733Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Into a 100-mL round-bottom flask was placed a solution of 113m (3.3 g, 12.30 mmol, 1.00 equiv) in ethanol (30 mL) and NiCl2.6H2O (3.2 g, 13.45 mmol, 1.10 equiv), followed by the addition of NaBH4 (1.4 g, 37.01 mmol, 3.00 equiv) in several batches at 0° C. (FIG. 14). The resulting solution was stirred at room temperature for 24 h. The solids were filtered out and the filtrate was concentrated under vacuum. The resulting solution was diluted with 30 mL of ethyl acetate and washed with 1×30 mL of hydrogen chloride (2 N). The solution was adjusted to pH=9 with saturated aqueous sodium bicarbonate and extracted with 2×30 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 0.7 g (21%) of 113n as a light yellow oil.

Aufarbeitung

  1. customInto a 100-mL round-bottom flask was placed
  2. filtrationThe solids were filtered out
  3. concentrationthe filtrate was concentrated under vacuum
  4. additionThe resulting solution was diluted with 30 mL of ethyl acetate
  5. washwashed with 1×30 mL of hydrogen chloride (2 N)
  6. extractionextracted with 2×30 mL of ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-484af358661445aa8501b87a1c3f87b1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115152B2

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