Potassium bisulfate → tert-Butyl (1-formylcyclopentyl)carbamate

HRID 2114839Notes

Reaction equation

HRID 2114839 reaction equation
CON(C)[C:4]([C:6]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>C1COCC1.O.CCOCC>[CH:4]([C:6]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

7

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 86612118HCID 86612118, compound

Product 1

HCID 16217741tert-Butyl (1-formylcyclopentyl)carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 1-{[methoxy(methyl)amino]carbonyl}-cyclopentylcarbamate (3.34 g, 12.27 mmol) in anhydrous THF (112 mL) at 0° C. under an atmosphere of nitrogen was added LAH (698 mg, 18.40 mmol), portionwise. The reaction was stirred at 0° C. for 30 min, treated with KHSO4 (3.4 g) in water (72 mL), diluted with Et2O, and stirred for 5 min. The layers were separated, and the aqueous was extracted with Et2O three times more. The combined organic extracts were washed twice each with aqueous 1N HCl solution, saturated aqueous NaHCO3 solution, and brine, dried over MgSO4, and concentrated in vacuo to afford the product as a sticky solid.

Workup

  1. stirringstirred for 5 min
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with Et2O three times more
  4. washThe combined organic extracts were washed twice each with aqueous 1N HCl solution, saturated aqueous NaHCO3 solution, and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d69914b860444c10984f8737faca2aac
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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