Water → (1-Benzylpyrrolidine-2,5-diyl)dimethanol

HRID 1650283Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH:18]([C:19](OCC)=[O:20])[CH2:17][CH2:16][CH:15]1[C:24](OCC)=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH:18]([CH2:19][OH:20])[CH2:17][CH2:16][CH:15]1[CH2:24][OH:25])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (10.25 g) in tetrahydrofuran (550 ml) was added dropwise a solution of 1-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine (55 g) in tetrahydrofuran (100 ml). The reaction mixture was stirred for 30 minutes at 0° C., allowed to warm to room temperature and then stirred at the same temperature for 1 hour. And then water was added carefully until excess lithium aluminum hydride was decomposed. After the precipitate was filtered off, the filtrate was evaporated under reduced pressure to give crude 1-benzyl-2,5-bis(hydroxymethyl)pyrrolidine (38.52 g).

Workup

temperatureto warm to room temperature
stirringstirred at the same temperature for 1 hour
filtrationAfter the precipitate was filtered off
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-fcde91b78bf9478ab1fa5f5dcdaa2c97
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923857

Reaction notes

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