Triethylamine → 1-Benzyl 3-methyl azetidine-1,3-dicarboxylate

HRID 1958676Notes

Reaction equation

HRID 1958676 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:9][NH:8][CH2:7]1)=[O:5].C(N(CC)CC)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(Cl)Cl>[N:8]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:9][CH:6]([C:4]([O:3][CH3:2])=[O:5])[CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 21100040Methyl azetidine-3-carboxylate hydrochloride

Product 1

HCID 450725021-Benzyl 3-methyl azetidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g of azetidine-3-carboxylic methyl ester hydrochloride and then 23 ml of triethylamine are added to 150 ml of CH2Cl2. The mixture is cooled and 13.5 g of benzyl chloroformate are added. After leaving overnight at AT, washing is carried out with water and then with HCl (N). After drying, concentrating to dryness and purifying by chromatography on silica (eluent: heptane-AcOEt (gradient from 0% to 50%)), 13.1 g of the expected compound are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. customAfter leaving overnight at AT
  3. washwashing
  4. customAfter drying
  5. concentrationconcentrating to dryness
  6. custompurifying by chromatography on silica (eluent: heptane-AcOEt (gradient from 0% to 50%)), 13.1 g of the expected compound
  7. customare obtained

Sources & evidence

ORD record
ord-5fd37fb0346845d19ef9c506ffa14fb7
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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