4-Methylmorpholine → HCID 688299, 화합물

HRID 2279455노트

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HRID 2279455 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC.Cl.[CH3:30][O:31][NH:32][CH3:33]>C(Cl)Cl>[CH3:30][O:31][N:32]([CH3:33])[C:13]([C@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15]

참가 물질

6

반응물 4

HCID 79724-Methylmorpholine2회HCID 10928Ethyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

생성물 1

HCID 688299HCID 688299, 화합물수율 68.03%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (11.93 g, 55.42 mmol) and DCM (70 mL) cooled to −15° C. was added a solution of NMM (5.79 g, 57.3 mmol), ethyl carbonochloridate (12.03 g, 110.8 mmol) and DCM (50 mL) and the mixture was stirred for 15 min. Additional NMM (11.59 g, 114.5 mmol) was added followed by portion wise addition of O,N-dimethylhydroxylamine hydrochloride (10.81 g, 110.8 mmol). The reaction was stirred at RT for 18 h. The reaction was poured onto water and extracted with DCM. The organic layer was dried, filtered, and concentrated and the crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane (1:1) to afford 9.74 g (68.03%) of (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (74).

후처리

  1. stirringThe reaction was stirred at RT for 18 h
  2. additionThe reaction was poured onto water
  3. extractionextracted with DCM
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude residue was purified by SiO2 chromatography
  8. washeluting with EtOAc/hexane (1:1)

출처 및 근거

ORD 기록
ord-00f5db4843c540a5bb5e8ebe5fdd1a15
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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