Pyrrolidine → Pyrrolidine, 1-(isocyanoacetyl)-

HRID 1824485Notes

Reaction equation

HRID 1824485 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-ea2b138349734d248107b41f92a0b9f6
Source dataset
uspto-grants-2006_05
Patent number
US07041831B2

Reaction notes

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