Potassium bisulfate → Benzyl (1-formylcyclopropyl)carbamate

HRID 84911Notes

Reaction equation

HRID 84911 reaction equation
CON(C)[C:4]([C:6]1([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>C1COCC1.O>[CH:4]([C:6]1([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:8]1)=[O:5]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 71743478HCID 71743478, compound

Product 1

HCID 54500481Benzyl (1-formylcyclopropyl)carbamateYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate (1.34 g, 4.82 mmol) in THF (25 mL) at 0° C. was added LiAlH4 (366 mg, 9.64 mmol). After stirred at 0° C. for 30 min, it was poured to a solution of KHSO4 (1.9 g) in water (30 mL), extracted with EtOAc, organic layer was separated, washed with brine, dried and concentrated to give benzyl 1-formylcyclopropylcarbamate (820 mg).

Workup

  1. extractionextracted with EtOAc, organic layer
  2. customwas separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9adbcff94a464b5e84768a06b2be84ae
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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