Dimethylformamide → HCID 53831546, compound

HRID 1780449Notes

Reaction equation

HRID 1780449 reaction equation
C[Li].Br[C:4]1[CH:19]=[CH:18][C:7]2[C@:8]3([CH3:17])[C@@H:13]([CH2:14][CH2:15][C:6]=2[CH:5]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]3.C([Li])(C)(C)C.CN(C)[CH:27]=[O:28]>C(OCC)C.C1COCC1.CCCCC>[CH:27]([C:4]1[CH:19]=[CH:18][C:7]2[C@:8]3([CH3:17])[C@@H:13]([CH2:14][CH2:15][C:6]=2[CH:5]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]3)=[O:28]

Participants

8

Reactant 4

HCID 6228Dimethylformamide2×HCID 11119935HCID 11119935, compoundHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 53831546HCID 53831546, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium (1.5 mL, 2.1 mmol of a 1.4M solution in diethyl ether) was added to (4aR)-(10bR)-8-bromo-10b-methyl-1,2,3,4,-4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (0.500 g, 1.7 mmol) in 25 mL of anhydrous THF which had been cooled in a dry ice/isopropanol bath under nitrogen, and was stirred for 15 min before addition of t-butyllithium (2.0 mL, 3.4 mmol of a 1.7M solution in pentane.) After 30 min, dimethylformamide (0.4 mL) was added, and the mixture was allowed to warm to 0°, and additional dimethylformamide (0.2 mL) was added. The ice bath was removed and the reaction was quenched with 1N hydrochloric acid to make pH=2, and then the mixture was extracted with 10% isopropanol/chloroform. The combined organic extracts were washed well with water, dried over sodium sulfate, and evaporated. The resulting product was slurried in diethyl ether before recrystallizing from 50% ethyl acetate/hexane to give off-white crystals: mp 185°-189°. FD MS 243M+; Calcd for C15H17N1O2 : C, 74.05; H, 7.04; N, 5.76; Found: C, 73.85; H, 7.11; N, 5.91.

Workup

  1. temperaturehad been cooled in a dry ice/isopropanol bath under nitrogen
  2. temperatureto warm to 0°
  3. customThe ice bath was removed
  4. customthe reaction was quenched with 1N hydrochloric acid
  5. extractionthe mixture was extracted with 10% isopropanol/chloroform
  6. washThe combined organic extracts were washed well with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. custombefore recrystallizing from 50% ethyl acetate/hexane
  10. customto give off-white crystals

Sources & evidence

ORD record
ord-fd091959979c4a7f99b019fe708a495a
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

Loading…