Dicyclohexylcarbodiimide → HCID 86688939, 화합물

HRID 404679노트

반응식

HRID 404679 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:43]12[CH2:50][CH2:49][CH:46]([CH2:47][CH2:48]1)[C@@H:45](O)[CH2:44]2>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]([O:11][C@@H:45]2[CH:46]3[CH2:49][CH2:50][N:43]([CH2:48][CH2:47]3)[CH2:44]2)=[O:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 162439412-(4-Chlorophenyl)-2-(piperidin-1-YL)acetic acid

생성물 1

HCID 86688939HCID 86688939, 화합물수율 61.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-(4-Chlorophenyl)-2-(piperidin-1-yl)acetic acid (190 mg, 0.75 mmol), DCC (309 mg, 1.50 mmol), and HOBT (229 mg, 1.50 mmol) were dissolved in dry THF (8 ml). (R)-quinuclidin-3-ol (286 mg, 2.25 mmol) was added and the reaction was stirred at room temperature for 16 hours. THF was evaporated and the residue was dissolved in EtOAc and washed with 1M NaHCO3, water and brine. The organic layer was separated, dried over Na2SO4, filtered and evaporated. The crude compound was purified by flash chromatography (DCM/MeOH/NH4OH=9 5/5/0.1) to obtain (R)-quinuclidin-3-yl 2-(4-chlorophenyl)-2-(piperidin-1-yl)acetate (167 mg, 61.5% yield) as a colorless oil.

후처리

  1. customTHF was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with 1M NaHCO3, water and brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude compound was purified by flash chromatography (DCM/MeOH/NH4OH=9 5/5/0.1)

출처 및 근거

ORD 기록
ord-c521bf61654e4ff2ac1c45ed71425b28
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

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