Formaldehyde → HCID 54436131, compound

HRID 568786Notes

Reaction equation

HRID 568786 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C@@H:14]([CH3:17])[CH2:15][OH:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:18]=O.[BH4-].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[C@@H:14]([CH3:17])[CH2:15][OH:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 712Formaldehyde2×HCID 14798Sodium HydroxideHCID 4311764Sodium borohydride3×HCID 54393263HCID 54393263, compound

Product 1

HCID 54436131HCID 54436131, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 6.25 g of (0.026 mole) (S)-2-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-1-propanol in 50 ml of MeOH under argon was added 3.9 ml (0.052 mole) of 37% aqueous formaldehyde and 4.7 g of sodiumborohydride pellets added one at a time. The solution was stirred at RT for 24 hr. an additional 1.0 ml of 37% aqueous formaldehyde and 1.0 g of sodium borohydride were added and the solution stirred for an additional 2.5 hr. Enough glacial acetic acid was added to react with the sodium borohydride. The reaction was made basic by addition of 3N sodium hydroxide. The methanol was evaporated in vacuo and the residue was extracted three times with ether. The organics were washed with brine an dried (K2CO3). Evaporation of the solvent in vacuo gave 5.74 g of (S)-2-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]-1-propanol as an oil (87% yield).

Workup

  1. additionadded one at a time
  2. stirringthe solution stirred for an additional 2.5 hr
  3. customThe methanol was evaporated in vacuo
  4. extractionthe residue was extracted three times with ether
  5. washThe organics were washed with brine
  6. dry with materialan dried (K2CO3)
  7. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-f6f3994c3bec4f2985e41ce1c33d3379
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

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