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

HRID 1367237ノート

反応式

HRID 1367237 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-84147da71ee540f2a9dd29af4f9ce166
出典データセット
uspto-grants-2011_02
特許番号
US07893079B2

反応ノート

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