Diisopropylethylamine → 1-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

HRID 1367237

반응식

HRID 1367237 반응식
[CH2:1]([C:4]1([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH2:14]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C>CC#N>[CH2:1]([C:4]1([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8][N:7]([C:22]([O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:23])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 66972977Methyl 4-allylpiperidine-4-carboxylate

생성물 1

HCID 588931861-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of methyl 4-allylpiperidine-4-carboxylate from Step A (5.30 g, 24.2 mmol), N-(benzyloxycarbonyloxy)succinimide (7.25 g, 29.1 mmol), and N,N-diisopropylethylamine (12.7 mL, 72.7 mmol) in CH3CN (61 mL) was stirred for 16 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc (100 mL) and saturated NaHCO3 (100 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (2×100 mL). The combined organic extracts were concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 40:60, to give the title compound. MS: m/z=318 (M+1).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc (100 mL) and saturated NaHCO3 (100 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with EtOAc (2×100 mL)
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customto give a residue that
  7. customwas purified by silica gel chromatography
  8. washeluting with a gradient of hexane

출처 및 근거

ORD 기록
ord-84147da71ee540f2a9dd29af4f9ce166
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893079B2

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