Ammonium Chloride → HCID 86647903, compound

HRID 2040287Notes

Reaction equation

HRID 2040287 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1.[CH3:17][Li].[NH4+].[Cl-]>O1CCCC1.CCOCC>[OH:1][C:2]1([CH3:17])[CH2:3][CH2:4][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 40424027tert-Butyl [(4-oxocyclohexyl)methyl]carbamateHCID 178418348HCID 178418348, compound

Product 1

HCID 86647903HCID 86647903, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a vigorous stirring solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound.

Workup

  1. customat −78° C.
  2. additionAfter completion of the addition
  3. extractionThe resulting mixture was extracted with dichloromethane (100 ml, three times)
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customloaded onto an Analogix purification system, and it
  9. washwas eluted with 0-50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-891a9f5e0fc946bd924662d6f24787f1
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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