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

HRID 2204122ノート

反応式

HRID 2204122 の反応式
[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

参加物

6

反応物 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

生成物 1

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

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dc305335409844eb8b4b06b6fb052359
出典データセット
uspto-grants-2016_06
特許番号
US09365588B2

反応ノート

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