Formaldehyde → HCID 67388095, compound

HRID 912600Notes

Reaction equation

HRID 912600 reaction equation
[CH3:1]/[CH:2]=[C:3]1\[C@H:4]2[CH:11]=[C:10]([CH3:12])[CH2:9][C@@:8]\1([NH2:13])[C:7]1[CH:14]=[CH:15][C:16]([NH:18][C:6]=1[CH2:5]2)=[O:17].C=O.[CH2:21]1COCC1>C(O)(C)C>[CH3:21][NH:13][C@@:8]12[C:7]3[CH:14]=[CH:15][C:16](=[O:17])[NH:18][C:6]=3[CH2:5][C@@H:4](/[C:3]/1=[CH:2]\[CH3:1])[CH:11]=[C:10]([CH3:12])[CH2:9]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 9794806HCID 9794806, compound

Product 1

HCID 67388095HCID 67388095, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Huperzine A 10 mg, and 37% aqueous solution of formaldehyde were refluxed for 1 hour in 2 mL of isopropanol; the solvent was stripped in vacuo; THF (dry, 5 mL) and NaBH(OOCCH3)3 0.15 g were added, the reaction mixture was allowed to stir for 4 hours; and then filtered to remove solid substances. The filtrate was purified after concentrating on prep TLC (chloroform:methanol=9:1) to yield 6 mg of pure title compound. MS: 257 (M+1).

Workup

  1. filtrationand then filtered
  2. customto remove solid substances
  3. customThe filtrate was purified
  4. concentrationafter concentrating on prep TLC (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-9599b2cd90b744c3a7843efc80e66f10
Source dataset
uspto-grants-2011_09
Patent number
US08026251B2

Reaction notes

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