Hydrochloric Acid → 1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolin-3-ol

HRID 1907744ノート

反応式

HRID 1907744 の反応式
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:10]=2[O:9][CH2:8]1.C([Sn](CCCC)(Cl)Cl)CCC.C1([SiH3])C=CC=CC=1.Cl>COCCOC.C(Cl)Cl.O>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:1]3[CH2:5][CH2:4][C:3]([OH:6])=[CH:2]3)=[CH:15][C:10]=2[O:9][CH2:8]1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 8438PiperonalHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 982104-Hydroxypyrrolidine

生成物 1

HCID 867621701-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolin-3-ol収率 60.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of pyrrolidin-3-ol (0.539 g, 6.2 mmol) in ethyleneglycol dimethylether (DME) (5 mL) was treated with benzo[d][1,3]dioxole-5-carbaldehyde (272) (1.08 g, 7.2 mmol) and dibutyldichlorostannane (0.71 g, 2.3 mmol). After the suspension was stirred for 15 min at room temperature, phenylsilane (1.0 mL, 8.6 mmol) was added neat and the mixture was stirred for 18 h. The reaction mixture was diluted with DCM (50 mL), treated with 1N HCl (13 mL) and stirred for 30 min followed by dilution with H2O (50 mL) and DCM (50 mL). The aqueous layer was collected, basified with solid potassium carbonate (K2CO3), extracted with DCM, dried over MgSO4, filtered and concentrated to provide title compound 273 (0.82 g, 60% yield).

後処理

  1. stirringthe mixture was stirred for 18 h
  2. stirringstirred for 30 min
  3. customThe aqueous layer was collected
  4. extractionextracted with DCM
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-56b396e2d2164af2bb5b84ef4cbf2084
出典データセット
uspto-grants-2013_12
特許番号
US08598168B2

反応ノート

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