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

HRID 237297ノート

反応式

HRID 237297 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7e2371a239da41baa24014c01d9a06dc
出典データセット
uspto-grants-2014_02
特許番号
US08642583B2

反応ノート

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