Hydrochloric Acid → HCID 178483639, compound

HRID 1063648Notes

Reaction equation

HRID 1063648 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][C:18]#N)[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.Cl.CC[O:33]CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[N:7]([CH3:8])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH:18]=[O:33])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydrideHCID 178483638HCID 178483638, compound

Product 1

HCID 178483639HCID 178483639, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 10.14 g (36.17 mmol) of trans-[2-(4-cyanomethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester in 90 mL of CH2Cl2 were added 90 mL (108.5 mmol, 3 eq) of 1.2M DIBAH at −70-−78° C. The solution was stirred at that temperature for 4 h, 40 mL of 4M HCl were added carefully and the solution was slowly warmed to RT. Stirring was continued at RT for 10 min, and the substance was partioned between ether and 1M HCl. The organic phases were washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography with n-hexane: EtOAc 1:3 to yield 7.5 g (73%) of trans-methyl-{2-[4-(2-oxo-ethyl)-cyclohexyl]-ethyl}-carbamic acid tert-butyl ester.

Workup

  1. stirringStirring
  2. waitwas continued at RT for 10 min
  3. washThe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with n-hexane: EtOAc 1:3

Sources & evidence

ORD record
ord-b1c646c14c2942e9bf61f22f79598544
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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