[1,1'-Biphenyl]-4,4'-dicarboxaldehyde → 4'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde

HRID 989269

Reaktionsgleichung

Reaktionsgleichung von HRID 989269
[C:1]1([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C>[N:17]1([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:1]3[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=3)=[CH:10][CH:11]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

7

Edukt 4

HCID 6200[1,1'-Biphenyl]-4,4'-dicarboxaldehydeHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 23676153Sodium bis(acetyloxy)boranuidyl acetate

Produkt 1

HCID 98139384'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of biphenyl-4,4′-dicarbaldehyde (0.21 g), pyrrolidine (83 μL), and acetic acid (57 μL) in DCM (5 mL) was treated with sodium triacetoxyborohyride (0.34 g). After 16 hours, the resulting mixture was treated with 3M NaOH (1.5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified via preparative thin layer chromatography eluting with 5% MeOH/DCM to give the title compound (42.5 mg). 1H NMR (400 MHz, CDCI3)δ10.05 (s, 1 H), 7.94 (d, J=8.0, 2 H), 7.75 (d, J=8.0, 2 H), 7.60 (d, J=8.0, 2 H), 7.47 (d, J=8.0, 2 H), 3.72 (s, 2 H), 2.61 (br s, 4 H), 1.84 (br s, 4 H).

Aufarbeitung

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified via preparative thin layer chromatography
  5. washeluting with 5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-8d576f7fb8994452926dd1480695ef3d
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638967B2

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