Hydrochloric Acid → 1-methyl-1H-spiro[chromeno[4,3-b]pyrrole-4,4'-piperidine]

HRID 2204122노트

반응식

HRID 2204122 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].O=[C:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1.O.CC1C=CC(S(O)(=O)=O)=CC=1.ClC(Cl)C.Cl>>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]2[C:15]3([O:13][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[C:3]1=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 220904482-(1-Methyl-1H-pyrrol-2-yl)phenol

생성물 1

HCID 585518401-methyl-1H-spiro[chromeno[4,3-b]pyrrole-4,4'-piperidine]

반응 조건

온도
80 °C

실험 절차

A mixture of 2-(1-methylpyrrol-2-yl)phenol (1.20 g, 6.90 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (1.38 g, 6.93 mmol), 4-methylbenzenesulfonic acid hydrate (264 mg, 1.39 mmol), and dichloroethane (24 mL) was heated at 80° C. for 2 h. To the mixture was added HCl (1.7 mL of 4.0 M, 6.9 mmol) and the mixture was allowed to stir at 50° C. for 1 h. The mixture was cooled to 25° C. and was concentrated in vacuo. The residue was taken up in dichloromethane and was washed with saturated aqueous NaHCO3. The organic layer was dried over sodium sulfate and concentrated. Column chromatography (0-100% ethyl acetate/hexanes) on the residue gave 1-methyl-1H-spiro[chromeno[4,3-b]pyrrole-4,4′-piperidine]. ESI-MS m/z calc. 254.3, found 255.2 (M+1)+; Retention time: 1.51 minutes (3 min run).

후처리

  1. temperatureThe mixture was cooled to 25° C.
  2. concentrationwas concentrated in vacuo
  3. washwas washed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dc305335409844eb8b4b06b6fb052359
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365588B2

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