Nitrogen → HCID 14098149, compound

HRID 2414111Notes

Reaction equation

HRID 2414111 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.N#N.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]1[C:27]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[C:26]([CH3:34])[N:25]([CH2:35][CH3:36])[C:24]2[CH2:37][O:38][C:39](=[O:40])[C:23]1=2.BrBr.C1CCCCC=1.C1C[O:52]CC1>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]1[C:27]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[C:26]([CH3:34])[N:25]([CH2:35][CH3:36])[C:24]2[CH:37]([OH:52])[O:38][C:39](=[O:40])[C:23]1=2

Participants

8

Reactant 7

HCID 947NitrogenHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 8079CyclohexeneHCID 24408BromineHCID 9842599BAY R3401HCID 178418339Butyllithium

Product 1

HCID 14098149HCID 14098149, compound

Conditions

Temperature
-78 °C

Procedure

60 mmol of diisopropylamine in 100 ml of analytical grade tetrahydrofuran are initially taken. 50 mmol of butyllithium are added at a temperature of 0°C., under a stream of N2. Thereafter, the mixture is cooled to -78° C. and a solution of 50 mmol of isopropyl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine3-carboxylate (dissolved in THF) is added dropwise. The mixture is stirred for 15 minutes at -78° C., and this solution is pumped, with the aid of nitrogen, into a solution of 50 mmol of Br2 and 50 ml of THF, and immediately thereafter 50 mmol of cyclohexene are added and the mixture is allowed to warm up to room temperature and is evaporated down, the residue is dissolved in DMSO, and H2O is added until the mixture starts to become cloudy. The mixture is left to stand for 12 hours, and the product is precipitated with H2O, filtered off under suction and separated with 9:1 CHCl3 /MeOH over silica gel.

Workup

  1. temperatureto warm up to room temperature
  2. customis evaporated down
  3. dissolutionthe residue is dissolved in DMSO
  4. additionH2O is added until the mixture
  5. waitThe mixture is left
  6. waitto stand for 12 hours
  7. customthe product is precipitated with H2O
  8. filtrationfiltered off under suction
  9. customseparated with 9:1 CHCl3 /MeOH over silica gel

Sources & evidence

ORD record
ord-8d1a0db4a51a4d67a5914480230a1cdb
Source dataset
uspto-grants-1988_01
Patent number
US04721719

Reaction notes

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