Pyrrolidine → Pyrrolidine, 1-(isocyanoacetyl)-

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

Reactant 2

HCID 31268Pyrrolidine

HCID 547815Methyl isocyanoacetate

Product 1

HCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-Yield 98%

Procedure

To stirred and cooled (0° C.) methyl isocyanoacetate (96% technical grade, 5.0 g, 47.8 mmol) was slowly added in 0.75 h pyrrolidine (6.5 mL, 78 mmol). The mixture was stirred for 1.5 h with continued cooling and then concentrated. The resulting oil was co-evaporated twice from CH2Cl2:hexane to remove residual pyrrolidine. 2-Isocyano-1-(pyrrolidin-1-yl)ethanone BLE 04098 was obtained as a yellow solid (6.85 g, 98% yield) and used in the next step without purification.

Workup

stirringThe mixture was stirred for 1.5 h
temperaturewith continued cooling
concentrationconcentrated
customhexane to remove residual pyrrolidine

Sources & evidence

ORD record: ord-487971cbeee54a0abaa2d7580575f24e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629165B2

Reaction notes

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