Water → HCID 86603730, compound

HRID 226427Notes

Reaction equation

HRID 226427 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@@H:16]([NH:19][C:20]2[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][N:21]=2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].O.[OH-].[Na+]>C1COCC1>[OH:25][CH2:24][C:23]1[CH:28]=[CH:29][C:20]([NH:19][C@@H:16]2[CH2:17][CH2:18][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15]2)=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68961292HCID 68961292, compound

Product 1

HCID 86603730HCID 86603730, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

Lithium aluminium hydride (1.02 g) was added to a solution of methyl 6-{[(3R)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]amino}nicotinate (5.76 g) in THF (80 ml) with stirring at 5-15° C. under atmospheric pressure of nitrogen, and the reaction mixture was stirred at 5-20° C. for 3 hours. The reaction mixture was cooled at 5° C. and H2O (1 ml), 15% NaOH solution (1 ml) and H2O (3 ml) was added and the resultant mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was filtrated and the filtrate was dried over MgSO4. The solvent was evaporated in vacuo and the residue was chromatographed on silicagel eluting with AcOEt-MeOH (9:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give tert-butyl (3R)-3-{[5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate (1.82 g).

Workup

  1. stirringthe reaction mixture was stirred at 5-20° C. for 3 hours
  2. temperatureThe reaction mixture was cooled at 5° C.
  3. filtrationThe reaction mixture was filtrated
  4. dry with materialthe filtrate was dried over MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on silicagel
  7. washeluting with AcOEt-MeOH (9:1)
  8. additionThe eluted fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-40fa07822bcf45ba9e1cfa583907f55a
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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