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

HRID 989269

반응식

HRID 989269 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8d576f7fb8994452926dd1480695ef3d
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638967B2

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