4-Methylmorpholine → 3-(2-Chlorobenzyloxy)-5-[1-N-(tert-butoxycarbonyl)piperidin-4-yl]toluene

HRID 482101노트

반응식

HRID 482101 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:32]=[CH:31][CH:30]=[CH:29][C:18]=1[CH2:19][O:20][C:21]1[CH:22]=C(O)[CH:24]=[C:25]([CH3:27])[CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCOCC1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:16][C:17]1[CH:32]=[CH:31][CH:30]=[CH:29][C:18]=1[CH2:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)[CH:22]=1

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 158950973-(2-Chlorobenzyloxy)-5-methylphenol

생성물 1

HCID 190649793-(2-Chlorobenzyloxy)-5-[1-N-(tert-butoxycarbonyl)piperidin-4-yl]toluene수율 70.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 177 mg (0.823 mmol) of N-tert-butoxycarbonyl-4-piperidinemethanol, as prepared in step f of Example 1, 195 mg (0.785 mmol) of 3-(2-chlorobenzyloxy)-5-methylphenol, as prepared in the preceding step, 262 mg (1.02 mmol) of triphenylphosphine, and 250 μL (2.27 mmol) of N-methylmorpholine in 3 mL of tetrahydrofuran was added 140 μL (0.892 mmol) of diethyl azodicarboxylate. The reaction mixture was stirred overnight, quenched with saturated NaCl (50 mL), and extracted into ethyl acetate (50 mL). The organic extract was dried (MgSO4), and the product was partially purified by flash chromatography (ethyl acetate/hexane (1:4)), to give 230 mg of impure title compound (contaminated with 3-(2-chlorobenzyloxy)-5-methylphenol). This material was used as is in the next reaction.

후처리

  1. customquenched with saturated NaCl (50 mL)
  2. extractionextracted into ethyl acetate (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customthe product was partially purified by flash chromatography (ethyl acetate/hexane (1:4))

출처 및 근거

ORD 기록
ord-724f5fb9a4a34f08bcd6991c653332d5
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792769

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