N-Methylpiperidine → HCID 178502741, 화합물

HRID 271348노트

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HRID 271348 반응식
[C:1]([O:5][C:6]([CH2:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCCCC1.ClC(OCC(C)C)=O.Cl.[CH3:32][NH:33][O:34][CH3:35]>ClCCl>[C:1]([O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([C:13](=[O:15])[N:33]([O:34][CH3:35])[CH3:32])[CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178451083HCID 178451083, 화합물

생성물 1

HCID 178502741HCID 178502741, 화합물수율 99.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To an ice cold solution of 1.74 g of cis-3-tert-butoxycarbonylmethyl-cyclobutanecarboxylic acid, 3 mL of N-methyl-piperidine, and 50 mL of dichloromethane was added 1.7 mL of isobutyl chloroformate drop-wise over 5 min. After an additional 5 min, 1.6 g of N-methyl-N-methoxy-amine hydrochloride was added and the mixture allowed to warm with stirring overnight. The resulting mixture was diluted with 100 mL of dichloromethane, washed with 100 mL of water, 100 mL of 0.1 N HCl, 50 mL of saturated sodium carbonate and dried over magnesium sulfate. The solution was diluted with 50 mL of toluene and concentrated under reduced pressure. Drying under vacuum overnight gave 2.08 g of product as a colorless thick oil: MS (m+1)=258.3; 1H NMR (400 MHz, CDCl3) 3.62 (s, 3H), 3.16 (s, 3H), 2.35 (d, 2H), 2.0 (dd, 1H), 1.4 (s, 9H).

후처리

  1. temperatureto warm
  2. washwashed with 100 mL of water, 100 mL of 0.1 N HCl, 50 mL of saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. additionThe solution was diluted with 50 mL of toluene
  5. concentrationconcentrated under reduced pressure
  6. customDrying under vacuum overnight

출처 및 근거

ORD 기록
ord-07bb58247aac4a578401c1dacc1af987
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452893B2

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