Carbon Dioxide → HCID 178483639, compound

HRID 967212Notes

Reaction equation

HRID 967212 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C(=O)=[O:12].[C:14]([O:18][C:19](=[O:33])[N:20]([CH2:22][CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][C:31]#N)[CH2:26][CH2:25]1)[CH3:21])([CH3:17])([CH3:16])[CH3:15].Cl>C(Cl)Cl>[C:14]([O:18][C:19](=[O:33])[N:20]([CH3:21])[CH2:22][CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][CH:31]=[O:12])[CH2:26][CH2:25]1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 178483638HCID 178483638, compound

Product 1

HCID 178483639HCID 178483639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90.4 ml (108.5 mmol) of diisobutylaluminium hydride (1.2M in toluene) were dropped under stirring and dry-ice-cooling at −70° C. to −78° C., within 20 minutes, to a solution of 10.14 g (36.17 mmol) of crude trans-[2-(4-cyanomethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester in 90 ml of methylenechloride. The reaction mixture was stirred for 4 hours at −70° C. to −78° C. To this reaction mixture was then carefully added 40 ml of 4N HCl (in water), within 10 minutes at −78° C. The temperature was slowly raised to room temperature. After stirring for 10 minutes at room temperature, the reaction mixture was partitioned between ether, 1N HCl and water. The ether-phase was dried over sodium sulfate and concentrated under reduced pressure giving 10.14 g of crude trans-methyl-{2-[4-(2-oxo-ethyl)-cyclohexyl]-ethyl}-carbamic acid tert-butyl ester as colorless oil, which was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours at −70° C. to −78° C
  2. stirringAfter stirring for 10 minutes at room temperature
  3. customthe reaction mixture was partitioned between ether, 1N HCl and water
  4. dry with materialThe ether-phase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2399bf8ec524c02b7bc77faeb533a8d
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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