Pyrrolidine → Pyrrolidine, 1-(isocyanoacetyl)-

HRID 2308380Notes

Reaction equation

HRID 2308380 reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>>[N+:1]([CH2:3][C:4]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:6])#[C-:2]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 547815Methyl isocyanoacetate

Product 1

HCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-Yield 96.1%

Procedure

To a stirred and cooled (0° C.) methyl isocyanoacetate (technical grade, 95%; 5.00 g, 47.8 mmol) was slowly added pyrrolidine (6.5 ml, 78 mmol). The mixture was stirred overnight with continued cooling and then concentrated. The resulting oil was repeatedly coevaporated from methylene chloride/hexane to remove residual pyrrolidine. Crude product, which was used in the next step without further purification, was thus afforded as 6.35 g (96%) of dark brown oil: 1H NMR (CDCl3) δ 4.24 (s, 2H), 3.53 (t, J=6.8, 2H), 3.41 (t, J=6.8, 2H), 2.02 (quintet, J=6.8, 2H), 1.90 (quintet, J=6.8, 2H) ppm.

Workup

  1. stirringThe mixture was stirred overnight
  2. temperaturewith continued cooling
  3. concentrationconcentrated
  4. customto remove residual pyrrolidine
  5. customCrude product, which was used in the next step without further purification

Sources & evidence

ORD record
ord-84c60141cb5b4267ab34f40d6e553daf
Source dataset
uspto-grants-2004_12
Patent number
US06835831B2

Reaction notes

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