Acetic Anhydride → tert-Butyl (1R*,4R*)-4-acetamidocyclohexylcarbamate

HRID 2386673Notes

Reaction equation

HRID 2386673 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17](OC(C)=O)=[O:18]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:17](=[O:18])[CH3:16])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

Product 1

HCID 66955585tert-Butyl (1R*,4R*)-4-acetamidocyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled suspension of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (15 g) in DCM (300 mL) was added Ac2O (10.8 mL) followed by TEA (2.19 mL), and the resulting mixture was stirred at RT for 3 h. The reaction mixture was then partitioned between DCM and water, and isopropyl amine was added to facilitate the separation. The organic layer was washed with dilute aqueous NaHCO3, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was triturated with Et2O, the solid was collected by filtration and dried under reduced pressure to afford 14.3 g of (4-acetylamino-cyclohexyl)-carbamic acid tert-butyl ester.

Workup

  1. customThe reaction mixture was then partitioned between DCM and water, and isopropyl amine
  2. additionwas added
  3. customthe separation
  4. washThe organic layer was washed with dilute aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with Et2O
  9. filtrationthe solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-3cd38751329c4550b9a29d0e795a8acf
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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