Ammonium formate → 1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(3-pyridylmethyl)piperidine

HRID 862735ノート

反応式

HRID 862735 の反応式
C(O[CH:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]23[CH2:33][CH:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=42)[C:25]2[C:20]3=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:14][CH2:13]1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)(=O)C.C([O-])=O.[NH4+]>[Pd].CO>[CH:21]1[C:20]2[C:19]3([CH2:18][N:15]4[CH2:14][CH2:13][CH:12]([CH2:5][C:6]5[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=5)[CH2:17][CH2:16]4)[CH2:33][CH:26]([C:27]4[C:32]3=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25]=2[CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 2

HCID 2723923Ammonium formate2 回HCID 231850921-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)4-piperidyl]-1-(3-pyridyl)methanol acetate

生成物 1

HCID 196986881-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(3-pyridylmethyl)piperidine収率 66%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of 1-[1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidyl]-1-(3-pyridyl)methanol acetate, prepared as in Example 53, (175 mg, 0.40 mmol), ammonium formate (175 mg, 2.78 mmol), and 10% palladium on carbon (175 mg) were heated to reflux in methanol (6 mL) under nitrogen (g) for 8 h. Additional ammonium formate (175 mg, 2.78 mmol) was added and heating was continued for an additional 8 h. The suspension was filtered through celite and the solids were washed thoroughly with methanol and ethyl acetate. Concentration of the filtrate left an off white foam. Flash chromatography on silica using 3% methanol/dichloromethane gave the title compound as a colorless glass (100 mg, 0.26 mmol, 66%). This was dissolved in methanolic hydrogen chloride and concentrated from methanol (3×100 mL) to give the hydrochloride salt, mp 183°-185° C.

後処理

  1. temperaturewere heated
  2. temperatureheating
  3. filtrationThe suspension was filtered through celite
  4. washthe solids were washed thoroughly with methanol and ethyl acetate
  5. waitConcentration of the filtrate left an off white foam

出典と根拠

ORDレコード
ord-3f3bac06af41484990a1da83fc22dcad
出典データセット
uspto-grants-1998_02
特許番号
US05719166

反応ノート

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