Ethyl Acetate → 5-(2-Hydroxy-3-pyrrolidin-1-yl-propoxy)-6-methoxy-indan-1-one

HRID 460348

Reaction equation

HRID 460348 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[O:13][CH2:14][CH:15]1[CH2:17][O:16]1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(OCC)(=O)C>COCCOC>[OH:16][CH:15]([CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:14][O:13][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:3]=1[O:2][CH3:1])[C:9](=[O:12])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 184458206-Methoxy-5-oxiranylmethoxy-indan-1-one2×

Product 1

HCID 184456745-(2-Hydroxy-3-pyrrolidin-1-yl-propoxy)-6-methoxy-indan-1-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 6-methoxy-5-oxiranylmethoxy-indan-1-one (Intermediate M, 2.5 g, 0.0106 mole) and pyrrolidine (0.9 mL, 0.011 mole) was stirred in 50 mL of DME at 50° C. for 5 hrs under Argon. Then, 150 mL of ethyl acetate was added and the solution washed with water (2×). Following extraction with 2N HCl, the aqueous acidic layer was made basic with 3N NaOH and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was triturated with diethyl ether to yield the title compound. MS m/z 306 (M+H)+.

Workup

  1. washthe solution washed with water (2×)
  2. extractionextraction with 2N HCl
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed in vacuo
  7. customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-6b9320af5adf4050b3d570a13ed95a33
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Linked notes

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