Water → HCID 68567173, compound

HRID 1970029Notes

Reaction equation

HRID 1970029 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-]>[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]1[CH2:17][CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinal

Product 1

HCID 68567173HCID 68567173, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

1.9 mL (6 mmol) of titanium isopropoxide and 1 g (10 mmol) of (R)-1-tert-butoxycarbonyl-pyrrolidine-2-carbaldehyde are added to a solution of 1 mL (30 mmol) of cyclopropylamine in 5 mL of anhydrous methanol. The solution is stirred for 5 hours at room temperature then 246 mg (605 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 1.17 g (97%) of (R)-1-tert-butoxycarbonyl-2-cyclopropylaminomethyl-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-5e60257e57414ee1a6d8431eeda2d397
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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