1,2-Dichloroethane → S-benzyl quinuclidine-3-carbothioate

HRID 1910523ノート

反応式

HRID 1910523 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)[CH2:3]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[C:34]1([CH2:40][SH:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[CH:4]([C:10](=[O:12])[S:41][CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:3]2

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

生成物 1

HCID 86672956S-benzyl quinuclidine-3-carbothioate収率 145.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Quinuclidine-3-carboxylic acid hydrochloride (55 mg, 0.29 mmol), EDC (83 mg, 0.43 mmol), and HOBT (65.9 mg, 0.43 mmol) were dissolved in dry THF (5 ml) under a nitrogen atmosphere. Triethylamine (140 μl, 1.00 mmol) and phenylmethanethiol (37.1 μl, 0.32 mmol) were dissolved in dry THF (2 ml) and then added to the reaction mixture. The resulting suspension was stirred at room temperature overnight. The mixture was evaporated, and the crude partitioned between EtOAc and water. The organic phase was washed with saturated NaHCO3, dried over sodium sulfate, filtered, and evaporated under vacuum to obtain S-benzyl quinuclidine-3-carbothioate (110 mg, crude), which was used in the next step without any further purification.

後処理

  1. additionadded to the reaction mixture
  2. customThe mixture was evaporated
  3. customthe crude partitioned between EtOAc and water
  4. washThe organic phase was washed with saturated NaHCO3
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

出典と根拠

ORDレコード
ord-1678ab116c804ac18bc15e53e8e0c41f
出典データセット
uspto-grants-2013_12
特許番号
US08604015B2

反応ノート

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