Bromine → HCID 13851311, compound

HRID 979157Notes

Reaction equation

HRID 979157 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][C@H:5]2[C:9]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=3[O:11][CH2:12][C@H:4]12.[Br:19]Br>C(O)(=O)C>[Br:19][C:13]1[C:10]2[O:11][CH2:12][C@@H:4]3[C@@H:3]([CH2:2][OH:1])[CH2:8][NH:7][CH2:6][C@H:5]3[C:9]=2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 13851309HCID 13851309, compound

Product 1

HCID 13851311HCID 13851311, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 8.66 g (±)-[4R*,4aS*,10bR*]-4-(hydroxymethyl)-1,3,4,4a,5,10b-hexahydro-9-methoxy-2H-[1]benzopyrano[4,3-c]pyridine in 90 ml acetic acid is added dropwise 1.96 ml bromine at 25°. After stirring 1.5 h, the solution is concentrated under reduced pressure and treated with 100 ml 2N NaOH. The aqueous phase is extracted with three 100 ml portions of CH2Cl2. The organic extracts are dried over Na2SO4, filtered, concentrated and flash chromatographed with CH2Cl2 /ammonia saturated methanol (90:10) to give the title compound as the major product; m.p. 281°-285° dec (HCl salt).

Workup

  1. concentrationthe solution is concentrated under reduced pressure
  2. additiontreated with 100 ml 2N NaOH
  3. extractionThe aqueous phase is extracted with three 100 ml portions of CH2Cl2
  4. dry with materialThe organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customflash chromatographed with CH2Cl2 /ammonia saturated methanol (90:10)

Sources & evidence

ORD record
ord-be9d034fb5ce442a94926e2e9e1018a9
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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