Water → tert-Butyl 3-(4-chlorobenzoyl)azetidine-1-carboxylate

HRID 1182097Notes

Reaction equation

HRID 1182097 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[O:7])[CH2:3]1.[C:15](=[O:18])(O)[O-:16].[Na+].O>O1CCOCC1.O>[C:4]([O:16][C:15]([N:2]1[CH2:5][CH:4]([C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:3]1)=[O:18])([CH3:6])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 69358091Azetidin-3-yl(4-chlorophenyl)methanone hydrochloride

Product 1

HCID 59446774tert-Butyl 3-(4-chlorobenzoyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
10 °C

Procedure

A solution of azetidin-3-yl-(4-chloro-phenyl)-methanone hydrochloride (50 g, 210 mmol) in dioxan:water 1:1 (800 ml) is added powdered sodium bicarbonate (61.7 g, 730 mmol) and the reaction mixture cooled to 10° C. Di-tbutyl-dicarbonate (52.6 g, 240 mmol) is added portion wise and the reaction mixture allowed to warm to room temperature with stirring for 1.5 hours. The reaction mixture is poured into water (1500 ml) and the resulting white precipitate filtered off and dried under vacuum to afford 3-(4-Chloro-benzoyl)-azetidine-1-carboxylic acid tert-butyl ester. 1H NMR 400 MHz, CDCl3, δ 1.45 (9H), 4.10 (1H), 4.20 (4H), 7.47 (2H), 7.80 (2H)

Workup

  1. temperatureto warm to room temperature
  2. filtrationthe resulting white precipitate filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-28918ffdc48b404180949dbca928ece8
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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