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

HRID 404643노트

반응식

HRID 404643 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-c118ea923fe34065b1a503a0f282f517
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

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