Ethyl Acetate → HCID 21710516, compound

HRID 650967Notes

Reaction equation

HRID 650967 reaction equation
CN(C1C2[C:10]([N:14]([CH3:16])C)=[CH:11][CH:12]=[CH:13][C:8]=2C=CC=1)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[C:28]([O:31]CC)(=[O:30])[CH3:29]>C(Cl)Cl>[CH2:21]([O:20][C:18]([N:14]1[CH2:10][CH2:11][CH:12]=[C:13]([CH2:8][O:31][C:28](=[O:30])[CH3:29])[CH2:16]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 88675Proton sponge

Product 1

HCID 21710516HCID 21710516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

This material is dissolved in 200 mL of methylene chloride. Proton sponge (2.5 mmol) is added in a single portion and the reaction mixture cooled to 0° C. Benzyl chloroformate (53 mmol) is added dropwise via addition funnel and the reaction mixture allowed to warm to room temperature. Stirring is continued for 2 hours at room temperature. The reaction mixture is diluted with ethyl acetate (200 mL) and washed with 1N hydrochloric acid (3×100 mL), water and brine. The organic layer is worked up to provide N-Benzyloxycarbonyl-3-acetoxymethyl-1,2,5,6-tetrahydropyridine. 1H NMR (CDCl3) δ7.40-7.25 (m, 5H), 5.90 (s, 1H), 5.14 (s, 2H), 4.47 (s, 2H), 3.95 (s, 2H), 3.54 (t, J=9.6Hz, 2H), 2.23-2.13 (m, 2H), 2.04 (s, 3H).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with 1N hydrochloric acid (3×100 mL), water and brine

Sources & evidence

ORD record
ord-5b34c79fac534f85ba93153bfc8a85cd
Source dataset
uspto-grants-2001_08
Patent number
US06277865B1

Reaction notes

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