Formaldehyde → HCID 13851321, compound

HRID 979158Notes

Reaction equation

HRID 979158 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[C@@H:15]([CH2:16][OH:17])[CH2:14][NH:13][CH2:12][C@H:11]3[C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1.[CH2:20]=O>C(O)=O>[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[C@@H:15]([CH2:16][OH:17])[CH2:14][N:13]([CH3:20])[CH2:12][C@H:11]3[C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 13851311HCID 13851311, compound

Product 1

HCID 13851321HCID 13851321, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1.65 g (±)-[4R*,4aS*,10bR*]-7-bromo-4-(hydroxymethyl)-1,3,4,4a,5,10b-hexahydro-9-methoxy-2H-[1]benzopyrano[4,3-c]pyridine in 0.5 ml 37% HCHO and 2.2 ml HCO2H is heated at 100° for 20 min. The reaction mixture is concentrated in vacuo and partitioned between 10 ml 2N NaOH and 50 ml CH2Cl2. The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure to yield the title compound; m.p. of HCl salt 262° dec.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompartitioned between 10 ml 2N NaOH and 50 ml CH2Cl2
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a6bd0327ebc4fcbb2a84712e58c171d
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

Loading…