Sodium Cyanide → tert-butyl (2R)-2-(cyanomethyl)pyrrolidine-1-carboxylate

HRID 1386021Notes

Reaction equation

HRID 1386021 reaction equation
CS(O[C@:6]1([CH3:18])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=O)=O.[C-:19]#[N:20].[Na+]>CN(C=O)C>[C:19]([CH2:18][C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])#[N:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86757172(R)-2-Methanesulfonyloxy-methyl-pyrrolidine-1-carboxylic acid, tert-butyl ester

Product 1

HCID 10727173tert-butyl (2R)-2-(cyanomethyl)pyrrolidine-1-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-2-methanesulfonyloxy-methyl-pyrrolidine-1-carboxylic acid, tert-butyl ester (D3) (90 g, 0.32 mol) in DMF (1200 ml) was added sodium cyanide (24 g, 0.49 mol). Heated to 60° C. overnight. Reaction mixture was concentrated and partitioned between water and ether. The organic phase was dried and concentrated to give the title compound (18 g, 30%) (M-Boc) 110.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. custompartitioned between water and ether
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e9d3ce2b88874421a88b078b734a74b2
Source dataset
uspto-grants-2001_07
Patent number
US06265408B1

Reaction notes

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