Aluminium lithium hydride → [1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-pyrrolidin-3-yl]-methanol

HRID 453844Notes

Reaction equation

HRID 453844 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=O)[N:7]([CH2:11][CH:12]2[O:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[O:17]1[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[O:14][CH2:13][CH:12]1[CH2:11][N:7]1[CH2:8][CH2:9][CH:5]([CH2:3][OH:2])[CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 667272991-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 62372448[1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-pyrrolidin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 130 mg (0.45 mmol) of 1-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester in dry tetrahydrofuran (4 mL) was added 68 mg (1.79 mmol) of LiAlH4. The reaction mixture was stirred at room temperature for 2½ h, and subsequently refluxed for 2 h. After the reaction mixture was cooled to room temperature, it was quenched with water and 1 M NaOH. The solution was filtered through celite and the filtrate was evaporated to dryness. Purification by column chromatography (silica gel, triethylamine/ethyl acetate, 1:99) afforded the title compound.

Workup

  1. temperaturesubsequently refluxed for 2 h
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customit was quenched with water and 1 M NaOH
  4. filtrationThe solution was filtered through celite
  5. customthe filtrate was evaporated to dryness
  6. customPurification by column chromatography (silica gel, triethylamine/ethyl acetate, 1:99)

Sources & evidence

ORD record
ord-3228913956fb45508929fbe086c84a0c
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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