Tetrahydrofuran → HCID 68041886, compound

HRID 869226Notes

Reaction equation

HRID 869226 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]1[CH2:20]OC[CH2:17]1.C([Li])(C)C>O>[CH: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)([CH3:20])[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 178506895HCID 178506895, compound

Product 1

HCID 68041886HCID 68041886, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of tert-butyl (4-oxocyclohexyl)carbamate (3.04 g) and THF (100 mL), isopropyllithium (0.7 M pentane solution) (40.3 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; n-hexane:ethyl acetate=3:1) and further purified (eluent; chloroform:methanol=30:1) to give tert-butyl (4-isopropyl-4-hydroxycyclohexyl)carbamate (Preparation Example 250) (0.854 g), which was a low-polarity product, as a white solid and tert-butyl (4-isopropyl-4-hydroxycyclohexyl)carbamate (Preparation Example 252) (0.179 g), which was a high-polarity product, as a yellow oil.

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; n-hexane:ethyl acetate=3:1)
  9. customfurther purified (eluent; chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-2e63cf6ddac745719cc52ece3afcf52f
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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