Dimethylformamide → (S)-1-[(S)-1-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)methyl]-3-methyl-piperidine-3-carboxylic acid ethyl ester

HRID 2366034노트

반응식

HRID 2366034 반응식
[CH2:1]([O:3][C:4]([C@@:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C@@H:14]1[CH2:23]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:3][C:4]([C@@:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][N:8]([CH2:23][C@@H:14]2[O:13][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][CH2:15]2)[CH2:7]1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 7101148(R)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonateHCID 23389262(S)-Ethyl 3-methylpiperidine-3-carboxylate

생성물 1

HCID 25176453(S)-1-[(S)-1-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)methyl]-3-methyl-piperidine-3-carboxylic acid ethyl ester수율 80.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

A mixture of (S)-ethyl-3-methylpiperidine-3-carboxylate (7.23 g, 42.2 mmol), Toluene-4-sulfonic acid (R)-1-(2,3-dihydro-benzo[1,4]dioxin-2-yl)methyl ester (15.0 g, 44.3 mmol), potassium carbonate (6.42 g, 46.4 mmol) and N,N-dimethyl formamide (50 ml) was heated to 120° C. After 4 hours the reaction mixture was cooled down, water (35 ml) was added and the mixture was extracted twice with ethyl acetate. The combined ethyl acetate layers were evaporated to dryness. Toluene (35 ml) was added to the evaporation residue and the mixture was extracted twice with 1M HCl. The combined acidic water layers were made basic with aq NaOH. The basic water layer was extracted twice with ethyl acetate and the combined ethyl acetate layers were evaporated to dryness to yield 10.8 g (76%) of the title compound.

후처리

  1. temperatureAfter 4 hours the reaction mixture was cooled down
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. customThe combined ethyl acetate layers were evaporated to dryness
  4. additionToluene (35 ml) was added to the evaporation residue
  5. extractionthe mixture was extracted twice with 1M HCl
  6. extractionThe basic water layer was extracted twice with ethyl acetate
  7. customthe combined ethyl acetate layers were evaporated to dryness

출처 및 근거

ORD 기록
ord-96417703f9b1430ebfc80281f398aada
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697723B2

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