Water → HCID 44182358, compound

HRID 2201660Notes

Reaction equation

HRID 2201660 reaction equation
[Br-].C1([C:8]([PH3+])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].O=C1CCC([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])CC1.O>O1CCCC1>[CH2:8]=[C:15]1[CH2:16][CH2:17][CH:18]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamate2×HCID 21951224Triphenylmethyl phosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 44182358HCID 44182358, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylmethylphosphonium bromide (53.7 g, 0.15 mol) was dissolved in 500 mL of tetrahydrofuran, potassium tert-butoxide (16.8 g, 0.15 mol) was added at −20° C., reacted for 0.5 h after the temperature was raised to 0° C. Then, tert-butyl 4-oxo-cyclohexylcarbamate (Compound 7-1) (21.3 g, 0.1 mol) was dissolved in 100 mL of THF and added dropwise into the flask under nitrogen. After 3 hours of reaction at room temperature, a small amount of water was added to dissolve the solids. The mixture was rotary evaporated to remove THF, extracted with anhydrous diethyl ether, and dried, concentrated, the concentrate was dissolved in n-hexane, and filtered by silica gel, then concentrated to give Compound 7-2 as a colorless liquid (19.5 g, 92.3% yield).

Workup

  1. customreacted for 0.5 h after the temperature
  2. additionadded dropwise into the flask under nitrogen
  3. customAfter 3 hours of reaction at room temperature
  4. dissolutionto dissolve the solids
  5. customThe mixture was rotary evaporated
  6. customto remove THF
  7. extractionextracted with anhydrous diethyl ether
  8. customdried
  9. concentrationconcentrated
  10. dissolutionthe concentrate was dissolved in n-hexane
  11. filtrationfiltered by silica gel
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a9e749d646d94e0fbf7b30baf03147e6
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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