Methanol → HCID 67385284, compound

HRID 905947Notes

Reaction equation

HRID 905947 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]1[CH2:13][C@@H:12]([CH3:14])[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].CO>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]1[CH2:13][C@@H:12]([CH3:14])[CH2:11][N:10]([C:22](=[O:24])[CH3:23])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 25068200HCID 25068200, compound

Product 1

HCID 67385284HCID 67385284, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((3R,5R)-5-Methyl-piperidin-3-yl)-carbamic acid tert-butyl ester (0.422 g, 1.971 mmol) was dissolved in DCM. Pyridine (0.2 mL, 2.56 mmol) was added, followed by acetic anhydride (0.24 mL, 2.56 mmol). The resulting colorless solution was stirred at RT overnight. 1 mL of MeOH was added and the mixture was stirred for about 30 minutes before being evaporated. The residue was partitioned between EtOAc and aqueous 1M HCl. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and evaporated. The remaining oil was dried under high vacuum to give 0.51 g of ((3R,5R)-1-acetyl-5-methyl-piperidin-3-yl)-carbamic acid tert-butyl ester as an off-white solid (>95% yield).

Workup

  1. stirringthe mixture was stirred for about 30 minutes
  2. custombefore being evaporated
  3. customThe residue was partitioned between EtOAc and aqueous 1M HCl
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe remaining oil was dried under high vacuum

Sources & evidence

ORD record
ord-ed8f80454fd74b9fa6e8f5afd65f587e
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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