Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate

HRID 404643ノート

反応式

HRID 404643 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])[CH2:4][C:3]1=[O:18].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46](O)[CH2:45]2>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([O:11][C@@H:46]2[CH:47]3[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]3)[CH2:45]2)=[O:10])[CH2:4][C:3]1=[O:18]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 584907532-(4-Methyl-3-oxopiperazin-1-yl)-2-phenylacetic acid

生成物 1

HCID 86688902(R)-quinuclidin-3-yl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-(4-Methyl-3-oxopiperazin-1-yl)-2-phenylacetic acid (170 mg, 0.68 mmol) was suspended in dry THF (6 ml) and DCC (283 mg, 1.37 mmol), HOBT (185 mg, 1.37 mmol) and (R)-quinuclidin-3-ol (174 mg, 1.37 mmol) were sequentially added. The reaction was stirred at room temperature for two days and then the insoluble was filtered off. The solution was evaporated and the residue was purified by flash chromatography (DCM/MeOH/NH4OH=96/4/0.4) to obtain (R)-quinuclidin-3-yl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate (175 mg, 54.1% yield over 2 steps) as a off-white spongy solid

後処理

  1. filtrationthe insoluble was filtered off
  2. customThe solution was evaporated
  3. customthe residue was purified by flash chromatography (DCM/MeOH/NH4OH=96/4/0.4)

出典と根拠

ORDレコード
ord-c118ea923fe34065b1a503a0f282f517
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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