Acetic Acid → tert-Butyl (3S)-3-(ethylamino)pyrrolidine-1-carboxylate

HRID 1970036Notes

Reaction equation

HRID 1970036 reaction equation
[CH:1](=O)[CH3:2].C([BH3-])#N.[Na+].C(O)(=O)C.[NH2:12][C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.C(=O)([O-])O.[Na+]>CO>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][C@H:13]([NH:12][CH2:1][CH3:2])[CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53346613tert-Butyl (3S)-3-(ethylamino)pyrrolidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

367 μL (6.5 mmol) of acetaldehyde, 817 mg (13 mmol) of sodium cyanoborohydride and 3.75 mL (65 mmol) of acetic acid are added to a solution of 1.47 mL (8.4 mmol) of (S)-3-amino-1-tert-butoxycarbonylpyrrolidine in 30 mL of anhydrous methanol. The solution is stirred at room temperature for 24 hours then a saturated aqueous solution of sodium hydrogencarbonate is added to adjust the pH to 7. The compound is extracted with ethyl acetate. The organic phases are dried over magnesium sulfate, filtered then evaporated and the residue is purified by chromatography on silica (eluent dichloromethane/methanol 94/6) to give 970 mg (70%) of (S)-1-tert-butoxycarbonyl-3-ethylamino-pyrrolidine in the form of a yellow oil.

Workup

  1. extractionThe compound is extracted with ethyl acetate
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. customthen evaporated
  5. customthe residue is purified by chromatography on silica (eluent dichloromethane/methanol 94/6)

Sources & evidence

ORD record
ord-c7744d834522441d9ff9145d1dde8688
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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