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

HRID 1814643

反応式

HRID 1814643 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒2 回HCID 65641,2-Dichloropropane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c4ba3e59128141eda86fbc76a7a03416
出典データセット
uspto-grants-2005_04
特許番号
US06875760B2

関連ノート

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