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

HRID 989269

Reaction equation

HRID 989269 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8d576f7fb8994452926dd1480695ef3d
Source dataset
uspto-grants-2003_10
Patent number
US06638967B2

Linked notes

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