Dimethylformamide → HCID 86740940, compound

HRID 364136Notes

Reaction equation

HRID 364136 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C@H:8]3[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH3:16])[C@@H:9]3[CH2:17][O:18][C:4]=2[C:3]=1[O:19][CH3:20].C([Li])CCC.CN(C)[CH:28]=[O:29]>O1CCCC1>[OH:29][CH2:28][C:2]1[CH:7]=[CH:6][C:5]2[C@H:8]3[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH3:16])[C@@H:9]3[CH2:17][O:18][C:4]=2[C:3]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 86740941HCID 86740941, compoundHCID 178418339Butyllithium

Product 1

HCID 86740940HCID 86740940, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 600 mg of trans-8-bromo-7-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine in 10 ml of tetrahydrofuran is treated with 1.68 ml of 2.1M n-butyllithium at -78°. After 10 minutes, 27 ml of dimethylformamide is added. After 30 minutes at 0°, the reaction mixture is poured onto water and the products are extracted with ether. After drying the solvent is removed. The residue is treated with 35 mg of sodium borohydride in 5 ml of methanol. After 10 minutes the solvent is removed and the residue is chromatographed on 10 g silica gel with acetone/hexane 1:2 as the eluent to afford trans-8-hydroxymethyl-7-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine.

Workup

  1. waitAfter 30 minutes at 0°
  2. additionthe reaction mixture is poured onto water
  3. extractionthe products are extracted with ether
  4. customAfter drying the solvent
  5. customis removed
  6. additionThe residue is treated with 35 mg of sodium borohydride in 5 ml of methanol
  7. customAfter 10 minutes the solvent is removed
  8. customthe residue is chromatographed on 10 g silica gel with acetone/hexane 1:2 as the eluent

Sources & evidence

ORD record
ord-1a8c89ee25b14ed4ac63705aced98aa4
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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