Water → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-hydroxymethyl-1-(phenylmethyl)pyrrolidine

HRID 1377760Notes

Reaction equation

HRID 1377760 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20](OC)=[O:21])[CH2:18][N:17]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.CCOCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([CH2:20][OH:21])[CH2:18][N:17]([CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70091886trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine

Product 1

HCID 70093734trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-hydroxymethyl-1-(phenylmethyl)pyrrolidineYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine (2.7 g, 6.6 mmol) in 27 mL of THF at 0° C. was added LiAlH4 (4.0 mmol, 4 mL of 1M toluene solution). After stirring for 2 hr the reaction mixture was then successively treated dropwise with H2O (0.15 mL), 15% NaOH (0.15 mL), and H2O (0.46 mL). The resulting suspension was diluted with ether, stirred for 1 hr, filtered through Celite, and concentrated under reduced pressure to an oil. Silica gel chromatography (graded elution: CH2Cl2 then 9:1, CH2Cl2 :methanol) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-hydroxymethyl-1-(phenylmethyl)pyrrolidine (2.0 g, 80%) as an oil.

Workup

  1. stirringstirred for 1 hr
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure to an oil
  4. washelution

Sources & evidence

ORD record
ord-a51a3e5017aa49629fec32ffd21cd11c
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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