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

HRID 1907744Notes

Reaction equation

HRID 1907744 reaction equation
[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

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-56b396e2d2164af2bb5b84ef4cbf2084
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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