Sodium cyanoborohydride → HCID 21525649, compound

HRID 1658880Notes

Reaction equation

HRID 1658880 reaction equation
[C:1]1([CH2:7][C:8](=O)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:15].[CH3:16]N.[C:18]([BH3-])#[N:19].[Na+]>CO>[ClH:15].[CH3:18][NH:19][CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:9][CH2:10][C:11]([O:13][CH3:16])=[O:12]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 10375311HCID 10375311, compound

Product 1

HCID 21525649HCID 21525649, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-phenyllevulinic acid (4.0 g, 206 mmoles), methylamine hydrochloride (6.75 g), sodium cyanoborohydride (1.0 g) and methanol (100 ml) was stirred at room temperature for 4 days, then acidified to pH 1.0 and evaporated to dryness. The residue was partitioned between water and ether, and the water phase was evaporated to dryness. The residue was extracted with dichloromethane (2 × 250 ml) which was then dried and evaporated. The residue was re-dissolved in dichloromethane, the solution filtered from some insolubles and evaporated. The residue was crystallized by a slow addition of ether to its solution in ethanol to give methyl 4-methylamino-5-phenylpentanoate hydrochloride. m.p. 117°-20°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and ether
  3. customthe water phase was evaporated to dryness
  4. extractionThe residue was extracted with dichloromethane (2 × 250 ml) which
  5. customwas then dried
  6. customevaporated
  7. dissolutionThe residue was re-dissolved in dichloromethane
  8. filtrationthe solution filtered from some insolubles
  9. customevaporated
  10. customThe residue was crystallized by a slow addition of ether to its solution in ethanol

Sources & evidence

ORD record
ord-be5003217e6b4d9c9cfa980b09ceca32
Source dataset
uspto-grants-1976_06
Patent number
US03966744

Reaction notes

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