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

HRID 2216373노트

반응식

HRID 2216373 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63d012b9370d4bfc8a38bdf549ded32d
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112593B2

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