Carbon tetrabromide → HCID 21994134, compound

HRID 1978307Notes

Reaction equation

HRID 1978307 reaction equation
O[CH2:2][CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:18][CH2:2][CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22594495tert-Butyl 4-(2-hydroxyethylidene)piperidine-1-carboxylate

Product 1

HCID 21994134HCID 21994134, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 15.292 g (67.277 mM) of tert-butyl 4-(2-hydroxyethylidene)piperidine-1-carboxylate and 24.5 g (74.0 mM) of carbon tetrabromide in 150 ml of acetonitrile was added 19.4 g (74.0 mM) of triphenylphosphine at −78° C. Then, at room temperature, the mixture was stirred for 2 hours. This reaction mixture was distilled under reduced pressure to remove the solvent. To the residue was added diethyl ether, followed by stirring, and the resulting precipitate was filtered off and washed with diethyl ether. The filtrate and washes were pooled and the solvent was distilled under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 9/1) to provide the title compound.

Workup

  1. distillationThis reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue was added diethyl ether
  4. stirringby stirring
  5. filtrationthe resulting precipitate was filtered off
  6. washwashed with diethyl ether
  7. distillationthe solvent was distilled under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 9/1)

Sources & evidence

ORD record
ord-c139d4020c2144efbb2109e30047cf0b
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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