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

HRID 1907744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907744
[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

Komponenten

9

Edukt 5

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

Produkt 1

HCID 867621701-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolin-3-olAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-56b396e2d2164af2bb5b84ef4cbf2084
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598168B2

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