Water → HCID 66569215, compound

HRID 1970030Notes

Reaction equation

HRID 1970030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]([NH2:18])([CH3:17])[CH3:16].[BH4-].[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:18][CH:15]([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 66569215HCID 66569215, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

1.9 mL (6 mmol) of titanium isopropoxide and 1 g (5 mmol) of (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carbaldehyde are added to a solution of 886 mg (15 mmol) of isopropylamine in 10 mL of anhydrous methanol. The solution is stirred for 5 hours at room temperature then 227 mg (6 mmol) of sodium borohydride is added. Stirring is continued for a further 2 hours then 2 mL of water is added. The reaction mixture is filtered then the solvents are evaporated. Water is added and the compound is extracted with diethyl ether. The organic phases are dried over magnesium sulfate, filtered and evaporated to give 1.05 g (86%) of (S)-1-tert-butoxycarbonyl-2-isopropylaminomethyl-pyrrolidine in the form of a colourless oil.

Workup

  1. stirringStirring
  2. waitis continued for a further 2 hours
  3. filtrationThe reaction mixture is filtered
  4. customthe solvents are evaporated
  5. additionWater is added
  6. extractionthe compound is extracted with diethyl ether
  7. dry with materialThe organic phases are dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-52af37120e9b43bc960e567eb400be88
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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