Formaldehyde → HCID 53737877, compound

HRID 264600Notes

Reaction equation

HRID 264600 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 at ambient temperature. To sodium bicarbonate solution (25 ml) and ice (25 g) was added reaction mixture gradually and was extracted with ethyl acetate (50 ml×2). The separated ethyl acetate layer was washed with brine,dried over anhydrous sodium sulfate and evaporated in vacuo. The resultant crude product was subjected to column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (7:3 by volume). The fractions containing the desired product were combined and evaporated in vacuo to give benzyl (R)-3-(4-dimethylaminophenyl)-2-hydroxypropionate (0.22 g).

Workup

  1. additionwas added gradually
  2. customreaction mixture gradually
  3. extractionwas extracted with ethyl acetate (50 ml×2)
  4. washThe separated ethyl acetate layer was washed with brine,dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. additionThe resultant crude product was subjected to column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (7:3 by volume)
  7. additionThe fractions containing the desired product
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba0b4377e1ba44f2aa60ec6c60f0c97d
Source dataset
uspto-grants-1997_07
Patent number
US05646244

Reaction notes

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