Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate

HRID 404666ノート

反応式

HRID 404666 の反応式
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:42]12[CH2:49][CH2:48][CH:45]([CH2:46][CH2:47]1)[C@@H:44](O)[CH2:43]2>C1COCC1>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][C@@H:44]1[CH:45]2[CH2:48][CH2:49][N:42]([CH2:47][CH2:46]2)[CH2:43]1)=[O:9]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 132542962-(2-Oxopyrrolidin-1-yl)-2-phenylacetic acid

生成物 1

HCID 86688927(R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate収率 93.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-(2-oxopyrrolidin-1-yl)-2-phenylacetic acid (345 mg, 1.57 mmol), DCC (649 mg, 3.15 mmol), HOBT (425 mg, 3.15 mmol) and (R)-quinuclidin-3-ol (400 mg, 3.15 mmol) in dry THF (15.7 ml) was stirred at room temperature for 24 hours. The yellow suspension was filtered washing the white solid with THF. The yellow solution was evaporated and the crude was purified by flash chromatography (DCM/MeOH=96/4+0.4% NH4OH) to collect the title compound (482 mg, 93% yield) as a pale yellow oil.

後処理

  1. filtrationThe yellow suspension was filtered
  2. washwashing the white solid with THF
  3. customThe yellow solution was evaporated
  4. customthe crude was purified by flash chromatography (DCM/MeOH=96/4+0.4% NH4OH)

出典と根拠

ORDレコード
ord-55d106f6108d44d5991f84052298f4e2
出典データセット
uspto-grants-2014_06
特許番号
US08748613B2

反応ノート

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