1,2-Dichloroethane → (4-Methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate

HRID 1910508

反応式

HRID 1910508 の反応式
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)O)=[CH:31][CH:30]=1>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:35]([C:32]1[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:34][CH:33]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:11])[CH2:3]2

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 953754-Methoxybenzhydryl alcoholHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

生成物 1

HCID 70925768(4-Methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate収率 13.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Quinuclidine-3-carboxylic acid hydrochloride (150 mg, 0.78 mmol), EDC (225 mg, 1.17 mmol), and HOBT (180 mg, 1.17 mmol) were dissolved in dry THF (7.5 ml). (4-Methoxyphenyl)(phenyl)methanol (184 mg, 0.86 mmol) and TEA (382 μl, 2.74 mmol) were added, and the resulting reaction was stirred at room temperature for four days. THF was removed under vacuum, and the crude residue was partitioned between EtOAc and water. The organic phase was washed with a sat. NaHCO3, dried over Na2SO4, filtered, and evaporated. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to EtOAc/MeOH=7:3+1% NH4OH) to give (4-methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate (37 mg, mixture of diastereoisomers). The compound was used as such in the next step.

後処理

  1. customthe resulting reaction
  2. customTHF was removed under vacuum
  3. customthe crude residue was partitioned between EtOAc and water
  4. washThe organic phase was washed with a sat. NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by flash chromatography (EtOAc/MeOH=8/2 to EtOAc/MeOH=7:3+1% NH4OH)

出典と根拠

ORDレコード
ord-f12da307f3d648fdbe9611e0ce06f43c
出典データセット
uspto-grants-2013_12
特許番号
US08604015B2

関連ノート

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