Dimethylformamide → HCID 59486383, compound

HRID 32080Notes

Reaction equation

HRID 32080 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[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[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:28]=[O:29])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10064926133277-10-8HCID 178418339Butyllithium

Product 1

HCID 59486383HCID 59486383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (Step C) (1.080 g, 3.311 mmol) was dissolved in THF (30 mL) and cooled to −78° C. n-Butyllithium (2.5 M) (3.311 mL, 8.276 mmol) was added drop-wise to the stirred solution. The reaction was stirred at −78° C. for 30 min and DMF (1.282 mL, 16.55 mmol) was added drop-wise and the mixture was slowly warmed to RT overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude material, which was purified by flash column chromatography to furnish the pure title compound. MS (APCI pos) 217 (M-t-Bu).

Workup

  1. additionwas added drop-wise to the stirred solution
  2. temperaturethe mixture 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 over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-fea7335b68e84aff8f79d6203751b877
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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