Ethyl Acetate → 3-(2-Methoxy-benzoyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 237297Notes

Reaction equation

HRID 237297 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12](=[O:17])N(OC)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Mg]Br)[CH3:19].OS([O-])(=O)=O.[K+].CCOC(C)=O>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12](=[O:17])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:18][CH3:19])[CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylateHCID 178489560HCID 178489560, compound

Product 1

HCID 584050543-(2-Methoxy-benzoyl)-azetidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(methoxy-methyl-carbamoyl)-azetidine-1-carboxylic acid tert-butyl ester (3.48 g, 14.2 mmol) in dry ether (150 mL) at 0° C. was added 2-methoxylphenylmagnesium bromide (1.0 M in THF, 17 mL, 17 mmol). The reaction was allowed to slowly warm to rt and stirred for 36 h. Then a solution of 1M KHSO4 and EtOAc were added and the aqueous portion was extracted once with EtOAc. The combined organic fractions were dried (Na2SO4) and concentrated to provide the title compound. This material was used in subsequent reactions without additional purifications. MS (ESI): mass calcd. for C16H21NO4, 291.1; m/z found, 236.1 [M-t-Bu]+. 1H NMR (CDCl3): 7.83 (dd, J=7.8, 1.8 Hz, 1H), 7.51 (ddd, J=8.5, 7.3, 1.8 Hz, 1H), 7.06-6.95 (m, 2H), 4.13-4.03 (m, 5H), 3.90 (s, 3H), 1.44 (s, 9H).

Workup

  1. extractionthe aqueous portion was extracted once with EtOAc
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7e2371a239da41baa24014c01d9a06dc
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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