Dimethylformamide → Tert-butyl 6-formylchroman-4-ylcarbamate

HRID 32071Notes

Reaction equation

HRID 32071 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=2)[O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN([CH:28]=[O:29])C>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:28]=[O:29])[CH:16]=2)[O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68930912HCID 68930912, compoundHCID 178418339Butyllithium

Product 1

HCID 86598502Tert-butyl 6-formylchroman-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(6-Bromo-chroman-4-yl)-carbamic acid tert-butyl ester (Step D) (3.859 g, 11.76 mmol) was dissolved in THF (50 mL) and cooled to −78° C. n-Butyllithium (2.5 M) (11.76 mL, 29.40 mmol) was added drop-wise to the stirred solution. The reaction mixture was stirred at −78° C. for 30 min and DMF (4.55 mL, 58.8 mmol) was added drop-wise and the system was slowly warmed to RT overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organics were dried with MgSO4 and concentrated in vacuo to afford the crude compound, which was purified by flash column chromatography to furnish the pure title compound.

Workup

  1. additionwas added drop-wise to the stirred solution
  2. temperaturethe system was slowly warmed to RT overnight
  3. customThe reaction was quenched with saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude compound, which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-ac27c7ff79c547979e078d979de09de2
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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