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

HRID 1910481

反応式

HRID 1910481 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.CCN(C(C)C)C(C)C.[F:36][C:37]1[CH:38]=[C:39]([CH:43]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=2)O)[CH:40]=[CH:41][CH:42]=1>CN(C=O)C.O>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:43]([C:39]1[CH:40]=[CH:41][CH:42]=[C:37]([F:36])[CH:38]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=1)=[O:11])[CH2:3]2

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2758250Bis(3-fluorophenyl)methanolHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

生成物 1

HCID 70925896Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate収率 57.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Quinuclidine-3-carboxylic acid hydrochloride (817 mg, 4.26 mmol), EDC (1.23 g, 6.39 mmol), and HOBT (979 mg, 6.39 mmol) were dissolved in dry DMF (40 ml). DIPEA (2.61 ml, 14.9 mmol) and bis(3-fluorophenyl)methanol (1.03 mg, 4.69 mmol) were added, and the mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted several times with Et2O. The organic phases were collected and washed with brine, dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (874 mg, racemic mixture).

後処理

  1. extractionextracted several times with Et2O
  2. customThe organic phases were collected
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (DCM/MeOH=9/1)

出典と根拠

ORDレコード
ord-e5b17f1598fd4752a8591a206b36f7cb
出典データセット
uspto-grants-2013_12
特許番号
US08604015B2

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