Ethanol → HCID 69348337, compound

HRID 336337Notes

Reaction equation

HRID 336337 reaction equation
[N@:1]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][CH:2]1[C:4]([O:6][CH3:7])=[O:5].B(F)(F)F.[CH3:22][CH2:23][O:24]CC.C(O)C>ClCCl>[CH2:11]([O:10][C:8]([NH:1][C@H:2]([C:4]([O:6][CH3:7])=[O:5])[CH2:3][O:24][CH2:23][CH3:22])=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8000Boron trifluoride etherateHCID 4255958154632-86-7

Product 1

HCID 69348337HCID 69348337, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-benzyl 2-methyl aziridine-1,2-dicarboxylate (prepared according to the literature procedure: Org. Biomol. Chem., 2005, 3, 3357, 2.7 g, 11.4 mmol) in dichloromethane (30 mL), boron trifluoride etherate (0.01 mL, 0.11 mmol) was added at 0° C. followed by absolute ethanol (1.05 g, 22.9 mmol). The reaction mixture was stirred at room temperature for an hour, after which the solution was quenched with saturated bicarbonate solution (2 mL), extracted with dichloromethane (3×25 mL), organic layers were washed with water (25 mL), brine solution (25 mL) and dried over sodium sulfate. The removal of solvents afforded crude product, which was purified by silica gel column chromatography using a gradient of ethyl acetate in pet. ether. Yield: 2.0 g (63%). 1H NMR (400 MHz, DMSO-d6) δ: 1.08 (t, 3H), 3.38-3.46 (m, 2H), 3.57-3.63 (m, 2H), 3.70 (s, 3H), 4.26-4.31 (m, 1H), 5.04 (s, 2H), 7.30-7.39 (m, 5H), 7.73 (d, 1H).

Workup

  1. customafter which the solution was quenched with saturated bicarbonate solution (2 mL)
  2. extractionextracted with dichloromethane (3×25 mL), organic layers
  3. washwere washed with water (25 mL), brine solution (25 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe removal of solvents
  6. customafforded crude product, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-78763c612a604196890b5813be9f7292
Source dataset
uspto-grants-2014_11
Patent number
US08889671B2

Reaction notes

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