1,2-Dichloroethane → Bis(4-chlorophenyl)methyl quinuclidine-3-carboxylate

HRID 1910483

反応式

HRID 1910483 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.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)O)=[CH:30][CH:29]=1>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:34]([C:31]1[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=1)[C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)=[O:11])[CH2:3]2

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 70334,4'-DichlorobenzhydrolHCID 757711-HydroxybenzotriazoleHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

生成物 1

HCID 70925824Bis(4-chlorophenyl)methyl quinuclidine-3-carboxylate収率 27.9%

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). Bis(4-chlorophenyl)methanol (218 mg, 0.86 mmol) was added followed by TEA (382 μl, 2.74 mmol). The resulting reaction was stirred at room temperature overnight. THF was removed under vacuum, and the crude was partitioned between EtOAc and water. The organic phase was washed with sat. NaHCO3, dried over sodium sulphate, filtered, and evaporated to dryness. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 7:3+1% of NH4OH) to obtain bis(4-chlorophenyl)methyl quinuclidine-3-carboxylate (85.0 mg, racemic mixture).

後処理

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

出典と根拠

ORDレコード
ord-5946ae15d1684747a1fe17c1f788fb08
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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