Ammonium Chloride → HCID 86647903, compound

HRID 1043223Notes

Reaction equation

HRID 1043223 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 aqueous NH4Cl solution. The resulting mixture was extracted with dichloromethane (3×100 mL) and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, 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 (3×100 mL)
  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
  9. washeluted with 0-50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-27b2f76d08684fa1af69f03b8afd815d
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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