Sodium Hydroxide → (2R,4R)-(+)-2-(hydroxymethyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidine

HRID 365331Notes

Reaction equation

HRID 365331 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C@H:12]1[CH2:16][C@@H:15]([O:17][CH2:18][O:19][CH3:20])[CH2:14][N:13]1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=O)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC.O>[OH:9][CH2:10][C@H:12]1[CH2:16][C@@H:15]([O:17][CH2:18][O:19][CH3:20])[CH2:14][N:13]1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 57141110(2R, 4R)-(+)-2-(ethoxycarbonyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidine

Product 1

HCID 54401947(2R,4R)-(+)-2-(hydroxymethyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidineYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled suspension of 690 mg of LiAlH4 (18.1 mmol) in 15 ml of dry ether was added 6.10 g (18.1 mmol) of (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl) pyrrolidine in 15 ml of dry ether and the mixture was stirred on ice for 30 min and at room temperature for 30 min. To the ice-cooled mixture 0.7 ml of water and 1N NaOH were added and the mixture was stirred for 30 min on ice, and for 30 min at room temperature. Magnesium sulfate was added and after stirring for 30 min, insoluble materials were filtered off on celite. The filtrate was concentrated in vacuo to give 5.30 g of (2R,4R)-(+)-2-(hydroxymethyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidine (99.3%) as pale yellow oil.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 30 min on ice
  3. waitfor 30 min at room temperature
  4. stirringafter stirring for 30 min
  5. filtrationinsoluble materials were filtered off on celite
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-be20ddee71774c1a9a2fef0bad67ef66
Source dataset
uspto-grants-2000_10
Patent number
US06127361

Reaction notes

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