Formaldehyde → HCID 53737877, compound

HRID 439572Notes

Reaction equation

HRID 439572 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([OH:20])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:4][CH:3]=1.C=O.[C:23]([BH3-])#[N:24].[Na+].[C:27](=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:27][N:24]([CH3:23])[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([OH:20])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 54490020HCID 54490020, compound

Product 1

HCID 53737877HCID 53737877, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of benzyl (R)-3-(4-aminophenyl)-2-hydroxypropionate (0.26 g) in acetic acid (6 ml) was added paraformaldehyde (0.3 g), and further sodium cyanoborohydride (0.3 g) was added gradually, and stirred for 3 hours. To the solution of sodium bicarbonate (25 ml) and ice (25 g) was added reaction mixture gradually and was extracted with ethyl acetate (50 ml×2). After washing the ethyl acetate layer with saturated brine, it was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the resultant crude product was purified by silica gel chromatography, and eluted with mixture of ethyl acetate and hexane (7:3, v/v). The fractions containing the desired product were combined and evaporated in vacuo to obtain benzyl (R)-3(4-dimethylaminophenyl)-2-hydroxypropionate (0.22 g). NMR (CDCl3,δ) 2.64 (d,1H),2.91 (s,6H),2.90 (dd,1H),3.04 (dd,1H),4.43 (ddd,1H), 5.18 (s,2H),6.63 (d,2H),7.01 (d,2H),7.35 (bs,5H)

Workup

  1. additionwas added gradually
  2. customreaction mixture gradually
  3. extractionwas extracted with ethyl acetate (50 ml×2)
  4. washAfter washing the ethyl acetate layer with saturated brine, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe resultant crude product was purified by silica gel chromatography
  8. washeluted with mixture of ethyl acetate and hexane (7:3
  9. additionThe fractions containing the desired product
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f06812e913c499dade9edd1f36f2e76
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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