Methyl isocyanoacetate → HCID 86626958, compound

HRID 1423899Notes

Reaction equation

HRID 1423899 reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].[NH:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1>CO>[OH:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:4](=[O:6])[CH2:3][N+:1]#[C-:2])[CH2:9]1

Participants

4

Reactant 2

HCID 547815Methyl isocyanoacetateHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 86626958HCID 86626958, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To stirred and cooled (0° C.) methyl isocyanoacetate (96% technical grade, 1.7 g, 17.21 mmol) was slowly added (R)-(+)-3-pyrrolidinol (1.5 g, 17.21 mmol) and MeOH (5 mL). The mixture was stirred for 3 h at RT and concentrated. Brine was added (30 mL) and the mixture was extracted with EtOAc (3×50 mL), dried over MgSO4, filtered and evaporated to obtained crude 1-((R)-3-hydroxypyrrolidin-1-yl)-2-isocyanoethanone VIB 01172 (1.3 g, 49% yield) as a yellow solid.

Workup

  1. stirringThe mixture was stirred for 3 h at RT
  2. concentrationconcentrated
  3. additionBrine was added (30 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-e5ddaa139f3445a1a277d63b9916c119
Source dataset
uspto-grants-2015_01
Patent number
US08927589B2

Reaction notes

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