Cyclohexanone → HCID 67343263, Verbindung

HRID 1669997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669997
[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 7967CyclohexanoneHCID 1519355(S)-1-Cbz-3-AminopyrrolidineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 67343263HCID 67343263, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of (3S)-1-Cbz-3-aminopyrrolidine (4.11 g, 16.0 mmol) and cyclohexanone (2.36 g, 24.0 mmol) in DCE (50 mL) was slowly added NaBH(OAc)3 (6.78 g, 32.0 mmol) at rt. The reaction mixture was quenched after 4 h using a saturated aqueous NaHCO3 solution and extracted with DCM followed by EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc/Hex=2/1) to give the title compound (4.79 g, 98.1%).

Aufarbeitung

  1. customat rt
  2. customThe reaction mixture was quenched after 4 h
  3. extractionextracted with DCM
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (EtOAc/Hex=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-604eb6d3055e48b4bf3e8a50446131a9
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989634B2

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