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

HRID 237297노트

반응식

HRID 237297 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-7e2371a239da41baa24014c01d9a06dc
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642583B2

반응 노트

불러오는 중…