Tetrahydrofuran → HCID 68041885, compound

HRID 869223Notes

Reaction equation

HRID 869223 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[CH2:16]1COC[CH2:17]1.C([Li])C>O>[CH2:16]([C:2]1([OH:1])[CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:6][CH2:7]1)[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 178506846HCID 178506846, compound

Product 1

HCID 68041885HCID 68041885, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of tert-butyl (4-oxocyclohexyl)carbamate (3.04 g) and THF (100 mL), ethyllithium (0.5 M benzene-cyclohexane solution) (56.8 mL) was added at −78° C. and stirred over 4 hours until it reached −50° C. After addition of water (150 mL), the reaction liquid was heated to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=30:1) and further purified (eluent; n-hexane:ethyl acetate=2:1 to 1:1) to give tert-butyl (4-ethyl-4-hydroxycyclohexyl)carbamate (Preparation Example 246) (0.202 g), which was a low-polarity product, as a white solid and tert-butyl (4-ethyl-4-hydroxycyclohexyl)carbamate (Preparation Example 248), which was a high-polarity product, as a colorless syrup.

Workup

  1. additionwas added at −78° C.
  2. customreached −50° C
  3. customthe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=30:1)
  9. customfurther purified (eluent; n-hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-46ab1a980d8949928f94f97dbccf31c0
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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