Water → (S)-2-Cyclopropylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1970028Notes

Reaction equation

HRID 1970028 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]1([NH2:18])[CH2:17][CH2:16]1.[BH4-].[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:15]1([NH:18][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 69828CyclopropylamineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 66569218(S)-2-Cyclopropylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 97.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

3.78 mL (13 mmol) of titanium isopropoxide and 2 g (10 mmol) of (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carbaldehyde are added to a solution of 1.7 mL (30 mmol) of cyclopropylamine in 10 mL of anhydrous methanol. The solution is stirred for 5 hours at room temperature then 378 mg (10 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 2.34 g (97%) of (S)—N-cyclopropyl-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethyl-amine 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-b8e06d809fd24216af73071447713306
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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