HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → 1-Benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidine

HRID 580562
Notes
Print preview

Reaction equation

HRID 580562 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][CH:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]([CH3:27])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>CCOCC>[CH2:7]([N:14]1[CH2:15][C@H:16]([CH3:27])[C@H:17]([NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19354327HCID 19354327, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 108808031-Benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidineYield 35.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (3.61 g) in absolute ether (150 ml) was added dropwise a solution of 1-benzyl-4-t-butoxycarbonylamino-3-methyl-2-oxopyrrolidine (14.46 g) in absolute ether (100 ml) with stirring for an hour at -5°~3° C. After stirring for an hour at 0° C., the reaction mixture as poured into ice-water and added 50% aqueous sodium hydroxide solution, the organic layer was separated, washed with water and saturated aqueous sodium chloride successively, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from acetonitrile to give the title compound (4.87 g) as colorless prisms, mp 134°-140° C.

Workup

  1. stirringAfter stirring for an hour at 0° C.
  2. customthe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0b0e004480d849979673175494dc8fdd
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04753953

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes