Lithium Chloride → HCID 13650110, compound

HRID 1761456Notes

Reaction equation

HRID 1761456 reaction equation
[C:1]([CH:3]1[CH2:5][N:4]1[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:15](OC)=[O:16])=[N:11][C:12]=1[O:13][CH3:14])#[N:2].[BH4-].[Na+].[Cl-].[Li+]>O1CCCC1>[OH:16][CH2:15][C:10]1[N:11]=[C:12]([O:13][CH3:14])[C:7]([CH2:6][N:4]2[CH2:5][CH:3]2[C:1]#[N:2])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 433294Lithium Chloride2×HCID 4311764Sodium borohydride2×HCID 13650109HCID 13650109, compound

Product 1

HCID 13650110HCID 13650110, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

247 mg. (1 mmol) methyl 5-[(2-cyano-1-aziridinyl)-methyl]-6-methoxypyridine-2-carboxylate (see Example 1) are dissolved in 10 ml. of anhydrous tetrahydrofuran and the solution is mixed with 74 mg. (2 mmol) sodium borohydride and 84 mg. (2 mmol) lithium chloride. After stirring for 12 hours at ambient temperature, the same amounts of sodium borohydride and lithium chloride are again added and, after a further 12 hours, the reaction mixture is mixed with 5 ml. water, evaporated and the residue taken up in ethanol and filtered. The filtrate is evaporated, the residue is taken up in acetone, filtered and evaporated. The residue is purified over a silica gel column (elution agent: acetone/toluene 1:3 v/v) (Rf value about 0.3) to give 120 mg. (55% of theory) of the desired product; m.p. 68°-70° C.

Workup

  1. additionthe reaction mixture is mixed with 5 ml
  2. customwater, evaporated
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified over a silica gel column (elution agent: acetone/toluene 1:3 v/v) (Rf value about 0.3)
  8. customto give 120 mg

Sources & evidence

ORD record
ord-c121503f304c4df3905c8192ee997759
Source dataset
uspto-grants-1989_05
Patent number
US04826858

Reaction notes

Loading…