Triethylamine → HCID 86626956, compound

HRID 1971282Notes

Reaction equation

HRID 1971282 reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].Cl.[F:9][C@H:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.C(N(CC)CC)C>CO>[F:9][C@H:10]1[CH2:14][CH2:13][N:12]([C:4](=[O:6])[CH2:3][N+:1]#[C-:2])[CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 547815Methyl isocyanoacetateHCID 16217739(s)-3-Fluoropyrrolidine hydrochloride

Product 1

HCID 86626956HCID 86626956, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To stirred and cooled (0° C.) methyl isocyanoacetate (96% technical grade, 1.18 g, 11.9 mmol) was slowly added (S)-(+)-3-fluoropyrrolidine hydrochloride (97%, 1.5 g, 11.9 mmol), triethylamine (1.67 mL, 11.9 mmol) and MeOH (3 mL). The mixture was stirred for 15 h at RT and concentrated. The mixture was stirred for 15 h at RT and concentrated. Water was added (50 mL) and the mixture was extracted with EtOAc (3×50 mL), dried over MgSO4, filtered and evaporated to obtained crude 1-((S)-3-fluoropyrrolidin-1-yl)-2-isocyanoethanone VIB 01166 (1.47 g, 79% yield) as a brown oil which was used in the next step without purification.

Workup

  1. stirringThe mixture was stirred for 15 h at RT
  2. concentrationconcentrated
  3. stirringThe mixture was stirred for 15 h at RT
  4. concentrationconcentrated
  5. additionWater was added (50 mL)
  6. extractionthe mixture was extracted with EtOAc (3×50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-d3e73c0bcb2240b9a89fc59c822e4a0b
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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