Benzyl chloroformate → HCID 67385303, compound

HRID 905950Notes

Reaction equation

HRID 905950 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].C([O-])(O)=O.[Na+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O1CCOCC1.O>[CH2:25]([O:24][C:22]([N:10]1[CH2:11][C@H:12]([CH3:14])[CH2:13][C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15])[CH2:9]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 25068200HCID 25068200, compound

Product 1

HCID 67385303HCID 67385303, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

((3R,5R)-5-Methyl-piperidin-3-yl)-carbamic acid tert-butyl ester (2.9 g, 13.53 mmol) was dissolved in 70 mL of a 1:1 mixture of dioxane and H2O and NaHCO3 (4.55 g, 54.13 mmol) was added. To the resulting suspension benzyl chloroformate (2.2 mL, 14.2 mmol) was added slowly. After 2 hours the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered, and evaporated. The remaining oil was purified by SiO2 chromatography (150 g SiO2, hexanes/EtOAc 0 to 20% EtOAc) to give 3.6 g of (3R,5R)-3-tert-butoxycarbonylamino-5-methyl-piperidine-1-carboxylic acid benzyl ester as a colorless oil (76% yield).

Workup

  1. additionwas added
  2. extractionAfter 2 hours the reaction mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe remaining oil was purified by SiO2 chromatography (150 g SiO2, hexanes/EtOAc 0 to 20% EtOAc)

Sources & evidence

ORD record
ord-ee91386002934f70a8f783be97eaa774
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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