Di-tert-butyl azodicarboxylate → HCID 59504796, compound

HRID 1517204Notes

Reaction equation

HRID 1517204 reaction equation
[N:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>O1CCCC1>[C:13]([O:12][C:10]([N:1]([CH:17]1[CH2:19][CH2:18]1)[NH:2][C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 97268Di-tert-butyl azodicarboxylateHCID 178418630HCID 178418630, compound

Product 1

HCID 59504796HCID 59504796, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of di-tert-butyl azodicarboxylate (115 g, 500 mmol) in tetrahydrofuran (1000 mL) was added to a cooled (−78° C.) solution of cyclopropylmagnesium bromide (2 M, 1000 mL, 500 mmol) in tetrahydrofuran. The reaction mixture was stirred at −78° C. for 10 minutes, After which time it was quenched onto acetic acid (30 mL) and allowed to warm to room temperature. This mixture was partitioned between water (2000 mL) and ethyl acetate (1500 mL). The organic extract was dried over sodium sulphate, filtered, and evaporated under reduced pressure to give a solid, which was purified by column chromatography eluting with 3.33% ethyl acetate in pentane to give the title compound as a white solid (45 g, 33%). 1H-NMR (400 MHz, CDCl3): δ 0.65 (m, 4H), 1.30-1.50 (m, 18H), 2.70 (m, 1H).

Workup

  1. customAfter which time it was quenched onto acetic acid (30 mL)
  2. temperatureto warm to room temperature
  3. customThis mixture was partitioned between water (2000 mL) and ethyl acetate (1500 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give a solid, which
  9. customwas purified by column chromatography
  10. washeluting with 3.33% ethyl acetate in pentane

Sources & evidence

ORD record
ord-eeef01a6350448899fbbd73f7b31b7e8
Source dataset
uspto-grants-2012_07
Patent number
US08232269B2

Reaction notes

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