Sodium Hydroxide → HCID 66657063, compound

HRID 660108Notes

Reaction equation

HRID 660108 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16](Cl)[CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>[C].[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66657090HCID 66657090, compound

Product 1

HCID 66657063HCID 66657063, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a 10 ml of ethanol solution containing 0.28 g of 3(S)-(3-chloro-4-methoxyphenylamino)pyrrolidine-1-carboxylic acid tert-butyl ester were added a 0.2 ml of a 5 N sodium hydroxide solution and 0.1 g of 10% palladium carbon. Catalytic reduction was conducted at room temperature and atmospheric pressure (ordinary pressure). The reaction solution was filtered using Celite and concentrated under reduced pressure. Water was added to the residue, and extraction with dichloromethane was performed. The extract was dried over magnesium sulfate and concentrated to dryness under reduced pressure to thereby obtain 0.25 g of yellow amorphous solid 3(S)-(4-methoxyphenylamino)pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customwas conducted at room temperature
  2. filtrationThe reaction solution was filtered
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue, and extraction with dichloromethane
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9c847201bb1046f08f72aed1890e3eac
Source dataset
uspto-grants-2011_12
Patent number
US08084442B2

Reaction notes

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