Formaldehyde → 3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-1-methyl-3-piperidinol

HRID 2216373ノート

反応式

HRID 2216373 の反応式
[CH2:1]([C:8]1[C:13]([C:14]#[C:15][C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=[C:10]([N:23]2[CH2:27][C@@H:26]([O:28][CH3:29])[C@H:25]([OH:30])[CH2:24]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([C:8]1[C:13]([C:14]#[C:15][C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][N:18]([CH3:33])[CH2:17]2)=[CH:12][CH:11]=[C:10]([N:23]2[CH2:27][C@@H:26]([O:28][CH3:29])[C@H:25]([OH:30])[CH2:24]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 98015133-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-3-piperidinol

生成物 1

HCID 102737293-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-1-methyl-3-piperidinol収率 81.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 94.0 mg of 3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-3-piperidinol (Example 1), 34.6 μl of an aqueous solution of 37% formaldehyde and 1.5 ml of dichloromethane was added 73.4 mg of sodium triacetoxyborohydride under ice-cooling, followed by stirring at room temperature for 30 minutes. The organic layer was separated by adding water and ethyl acetate to the reaction mixture, and then it was washed with an aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by NH-silica gel column chromatography with 5% methanol/ethyl acetate, to give 79.0 mg of the title compound.

後処理

  1. temperaturecooling
  2. customThe organic layer was separated
  3. additionby adding water and ethyl acetate to the reaction mixture
  4. washit was washed with an aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by NH-silica gel column chromatography with 5% methanol/ethyl acetate

出典と根拠

ORDレコード
ord-63d012b9370d4bfc8a38bdf549ded32d
出典データセット
uspto-grants-2006_09
特許番号
US07112593B2

反応ノート

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