Hydrochloric Acid → HCID 73424848, compound

HRID 1748739Notes

Reaction equation

HRID 1748739 reaction equation
[C:1](#[N:3])[CH3:2].C([Li])CCC.[N:9]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14](OC)=[O:15].Cl>C1COCC1.O>[C:1]([CH2:2][C:14]([C@@H:10]1[CH2:11][CH2:12][CH2:13][N:9]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])#[N:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 1277666Boc-L-Pro-OmeHCID 178418339Butyllithium

Product 1

HCID 73424848HCID 73424848, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of acetonitrile (1.5 mL, 29 mmol) in THF (60 mL) was added n-butyl lithium (2.5 M solution in hexane, 10.8 mL, 29 mmol) at −78° C. The solution was stirred at about −78° C. for about 10 min and a solution of 1-tert-butyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate (5.64 g, 25 mmol, US2007197506) in 15 mL of THF was added. The mixture was stirred at about −78° C. for about 1 hr and was subsequently allowed to reach rt (overnight). Water was added and the mixture acidified to pH 3 with 1N aqueous hydrochloric acid. The layers were separated and the organic layer was washed with water (10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to give tert-butyl (2S)-2-(2-cyanoacetyl)pyrrolidine-1-carboxylate (5.8 g, 24.3 mmol, 97%) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at about −78° C. for about 1 hr
  2. customto reach rt
  3. custom(overnight)
  4. customThe layers were separated
  5. washthe organic layer was washed with water (10 mL) and brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09bb4dd496ce43fd96c453271b1137f3
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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