Ammonium Chloride → HCID 86647903, compound

HRID 1036032Notes

Reaction equation

HRID 1036032 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-e188b430c9bd47828bdb6d86f85d19ea
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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