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

HRID 1864914Notes

Reaction equation

HRID 1864914 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-27d0204ce85642e7a436dd7cf0e87cd7
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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