Triethylamine → HCID 86251665, compound

HRID 1971281Notes

Reaction equation

HRID 1971281 reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].Cl.[F:9][C:10]1([F:15])[CH2:14][CH2:13][NH:12][CH2:11]1.C(N(CC)CC)C>CO>[F:9][C:10]1([F:15])[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 249034823,3-Difluoropyrrolidine hydrochloride

Product 1

HCID 86251665HCID 86251665, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To stirred and cooled (0° C.) methyl isocyanoacetate (96% technical grade, 345 mg, 3.48 mmol) was slowly added 3,3-difluoropyrrolidine hydrochloride (500 mg, 3.48 mmol), triethylamine (487 μL, 3.48 mmol) and MeOH (1 mL). The mixture was stirred for 15 h at RT and then concentrated. The resulting oil was coevaporated twice from EtOAc. 1-(3,3-Difluoropyrrolidin-1-yl)-2-isocyanoethanone VIB 01158 was obtained as a yellow oil (305 mg, 60% yield) and used in the next step without purification.

Workup

  1. stirringThe mixture was stirred for 15 h at RT
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-23b53a3e008c4e0ab0e53fe60d7156e6
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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