Potassium Carbonate → 4-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester

HRID 1814643

반응식

HRID 1814643 반응식
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]1(=[C:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)[CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCC(Cl)C.ClCCl.C(O)(=O)C>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH:26]2[CH2:27][CH2:28][C:23](=[C:20]3[CH2:22][CH2:21]3)[CH2:24][CH2:25]2)=[CH:7][CH:6]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 225021744-Cyclopropylidenecyclohexanone

생성물 1

HCID 235501404-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester수율 35%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회HCID 65641,2-Dichloropropane용매

실험 절차

4-Aminomethylbenzoic acid methyl ester, hydrochloride salt (2.2 g, 11 mmol) was suspended in 1,2 dichloropropane (30 mL) and an aqueous saturated solution of potassium carbonate (15 mL) was added. The next day the organic phase was isolated and dried (MgSO4). 4-Cyclopropylidenecyclohexanone (1.5 g, 11 mmol) dissolved in dichloromethane (15 mL) was added followed by addition of acetic acid (400 μL) and sodium triacetoxyborohydride (3.3 g, 16.5 mmol). After 72 hours at 20° C. the reaction mixture was diluted with dichloromethane (50 mL) and washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (50 g silica) using ethyl acetate and methanol (97:3) as eluent to give 1.1 g of 4-[(4-cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester.

후처리

  1. customThe next day the organic phase was isolated
  2. dry with materialdried (MgSO4)
  3. additionwas added
  4. washwashed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (50 g silica)

출처 및 근거

ORD 기록
ord-c4ba3e59128141eda86fbc76a7a03416
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875760B2

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