4-Phenylbutanal → HCID 70003138, compound

HRID 1952960Notes

Reaction equation

HRID 1952960 reaction equation
[Na].[ClH:2].[CH3:3][O:4][C:5](=[O:10])[C@@H:6]([CH2:8][OH:9])[NH2:7].[C:11]1([CH2:17][CH2:18][CH2:19][CH:20]=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([BH3-])#N.[Na+].Cl.CO>CO.C(O)(=O)C>[ClH:2].[CH3:3][O:4][C:5](=[O:10])[C@H:6]([NH:7][CH2:20][CH2:19][CH2:18][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][OH:9]

Participants

8

Reactant 5

HCID 290304-PhenylbutanalHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 11446470D-Serine methyl ester hydrochlorideHCID 21893726Hydrochloride methanol

Product 1

HCID 70003138HCID 70003138, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

2% Sodium in methanol (0.052 moles, 59.8 ml) is added to D-Serine methyl ester hydrochloride (0.052 moles, 8.16 g), dissolved in methanol (81.6 ml), to release the base. The formed sodium chloride is precipitated with ethyl ether (163 ml) and filtered off. The filtrate is evaporated to dryness under vacuum. The resulting residue is dissolved in methanol (150 ml), added with 4-phenylbutanal (0.051 moles, 10.69 g) and adjusted to pH 6 with acetic acid, added with sodium cyanoborohydride (0.055 moles, 3.62 g) and reacted at r.t. for 24 hours. The mixture is acidified with methanol HCl, evaporated to dryness under vacuum, taken up in methylene chloride (600 ml) and in a 1M sodium bicarbonate solution. The phases are separated and the aqueous one is extracted again with methylene chloride (3×200 ml), then the combined organic phases are washed with water and evaporated to dryness under vacuum. The product is recovered as the hydrochloride, taking up with ethyl ether (180 ml) and acidifying with ether HCl. The precipitated white solid is dried under vacuum at 30° C. Yield: 5.83 g (40%)

Workup

  1. customThe formed sodium chloride is precipitated with ethyl ether (163 ml)
  2. filtrationfiltered off
  3. customThe filtrate is evaporated to dryness under vacuum
  4. dissolutionThe resulting residue is dissolved in methanol (150 ml)
  5. customreacted at r.t. for 24 hours
  6. customevaporated to dryness under vacuum
  7. customThe phases are separated
  8. extractionthe aqueous one is extracted again with methylene chloride (3×200 ml)
  9. washthe combined organic phases are washed with water
  10. customevaporated to dryness under vacuum
  11. customThe product is recovered as the hydrochloride
  12. customThe precipitated white solid is dried under vacuum at 30° C

Sources & evidence

ORD record
ord-376ff8b26b464008a05431291b571a17
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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