Triethylamine → HCID 86626957, compound

HRID 1971283Notes

Reaction equation

HRID 1971283 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 2759162(3R)-3-fluoropyrrolidine hydrochloride

Product 1

HCID 86626957HCID 86626957, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To stirred and cooled (0° C.) methyl isocyanoacetate (96% technical grade, 0.79 g, 7.96 mmol) was slowly added (R)-(−)-3-fluoropyrrolidine hydrochloride (1.0 g, 7.96 mmol), triethylamine (1.11 mL, 7.96 mmol) and MeOH (2.5 mL). 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-((R)-3-fluoropyrrolidin-1-yl)-2-isocyanoethanone BLE 04170 as a brown oil (0.96 g, 77% yield) which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-a927f8056cba4a7289d17163a631509f
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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