Benzyl chloromethyl ether → HCID 67037408, compound

HRID 216053Notes

Reaction equation

HRID 216053 reaction equation
[Li+].CC([N-]C(C)C)C.[N:9]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1.[CH2:27](Cl)[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH2:29]([O:28][CH2:27][C:12]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10][N:9]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:14][CH2:13]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 137983Benzyl chloromethyl etherHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 67037408HCID 67037408, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LDA (2.64 mL, 5.82 mmol) was added to a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (1 g, 3.88 mmol) in THF (35 ML) at −78° C. The reaction was stirred for 30 min, and then BOMCl (0.6 g, 3.88 mmol) was added. The reaction was allowed to warm to room temperature, and then quenched with aq. NH4Cl. The aqueous layer was extracted with EtOAc, and the organic extract was washed with brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography (80 g SiO2, 0-10% ethylacetate:hexanes) to afford the title compound (0.5 g, 34%). MS (ES+) [M+H]+=378.

Workup

  1. customquenched with aq. NH4Cl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. extractionthe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography (80 g SiO2, 0-10% ethylacetate:hexanes)

Sources & evidence

ORD record
ord-ce303e00874e419b8b34dfff21a221cf
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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