Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

HRID 253547

반응식

HRID 253547 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:17][NH:18][O:19][CH3:20].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:13]([CH:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:15]

참가 물질

6

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

생성물 1

HCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (4.00 g, 18.6 mmol), N,O-dimethylhydroxylamine hydrochloride (1.69 g, 17.4 mmol), and DIEA (7.5 mL, 41.8 mmol) in CH2Cl2 (80 mL) was added solid EDC.HCl (4.00 g, 20.9 mmol). The mixture was stirred at rt for 18 h and concentrated under reduced pressure. The residue was taken up in ether (175 mL), washed with 5% aq HCl (2×50 mL) and satd aq NaHCO3 (50 mL), and dried over MgSO4. Removal of the solvent left tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (3.16 g, 65%) as an oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. washwashed with 5% aq HCl (2×50 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (3.16 g, 65%) as an oil

출처 및 근거

ORD 기록
ord-51b8c79eb25f4cb388926ab69e6be43e
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872028B2

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