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

HRID 1910483

반응식

HRID 1910483 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5946ae15d1684747a1fe17c1f788fb08
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

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