Acetic Acid → (R)-tert-Butyl 3-(cyclopropylamino)pyrrolidine-1-carboxylate

HRID 527904Notes

Reaction equation

HRID 527904 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(O[C:17]1(O[Si](C)(C)C)[CH2:19][CH2:18]1)C.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH:17]1([NH:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53346626(R)-tert-Butyl 3-(cyclopropylamino)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (400 mg, 2.15 mmol), (1-ethoxycyclopropoxy)trimethylsilane (1500 mg, 8.60 mmol) in methanol (30 mL) was added sodium cyanoborohydride (569 mg, 8.60 mmol) and acetic acid (0.2 mL). The mixture was stirred at reflux for 10 h. The volatiles were removed under reduced pressure. The residue was treated with water (20 mL) and extracted with ethyl acetate (3×30 mL). The combined extracts were washed with brine (3×10 mL), dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound. MS (m/z): 227 (M+H)+.

Workup

  1. temperatureat reflux for 10 h
  2. customThe volatiles were removed under reduced pressure
  3. additionThe residue was treated with water (20 mL)
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined extracts were washed with brine (3×10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-50725f1ae329487eaa7e8374aaab6e08
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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