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

HRID 2407343Notes

Reaction equation

HRID 2407343 reaction equation
C[O:2][C:3]([C:5]1([CH3:21])[CH2:9][CH2:8][N:7]([CH2:10][CH:11]2[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][CH2:12]2)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[O:16]1[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH:11]1[CH2:10][N:7]1[CH2:8][CH2:9][C:5]([CH2:3][OH:2])([CH3:21])[CH2:6]1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 251761241-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-methyl-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 25175667[1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-methyl-pyrrolidin-3-yl]-methanol

Procedure

The reduction of 84 mg (0.28 mmol) of 1-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-methyl-pyrrolidine-3-carboxylic acid methyl ester with 20 mg (0.53 mmol) of LiAlH4 was performed using the procedure described above. Purification by column chromatography (silica gel, methanol/triethylamine/dichloromethane, 1:1:99) yielded the desired pure alcohol.

Workup

  1. customPurification by column chromatography (silica gel, methanol/triethylamine/dichloromethane, 1:1:99)

Sources & evidence

ORD record
ord-2db84d32bd1d41ec86ec3d564618b9c4
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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