Triethylamine → (S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanone

HRID 545302노트

반응식

HRID 545302 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.Cl.[N:13]1([C@H:18]2[CH2:22][CH2:21][NH:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[N:13]1([C@H:18]2[CH2:22][CH2:21][N:20]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)=[O:8])[CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 671716781-[(3S)-pyrrolidin-3-yl]pyrrolidine dihydrochloride

생성물 1

HCID 59725829(S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-fluorobenzoic acid (3.5 g, 24.98 mmol) in DMF is treated with (S)-1,3′-bipyrrolidine dihydrochloride (10.65 g, 49.96 mmol), triethylamine (12.64 g, 124.90 mmol), 1-ethyl-3(3-dimethylaminopropyl)carbodiimide (5.75 g, 28.98 mmol) and N-hydroxybenzotriazole (4.05 g, 29.98 mmol), stirred at room temperature for 16 h and concentrated in vacuo. The resultant residue is partioned between CH2Cl2 and H2O. The organic phase is separated, washed sequentially with saturated NaHCO3 and brine, dried over MgSO4 and concentrated. The concentrate is absorbed onto silica and purified by flash column chromatography (10% methanol in CH2Cl2) to give the title product, identified by NMR and mass spectral analyses.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe organic phase is separated
  3. washwashed sequentially with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe concentrate is absorbed onto silica
  7. custompurified by flash column chromatography (10% methanol in CH2Cl2)

출처 및 근거

ORD 기록
ord-4a195029e5aa448ea5ee03f75c77d5fc
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935719B2

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