Di-tert-butyl azodicarboxylate → HCID 59593433, compound

HRID 2261476Notes

Reaction equation

HRID 2261476 reaction equation
C(OC(=O)N=NC(OC(C)(C)C)=O)(C)(C)C.[Si:17]([O:34][C@H:35]([CH2:45][CH2:46]O)[C:36]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37])([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[Si:17]([O:34][C@@H:35]1[CH2:45][CH2:46][N:38]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:36]1=[O:37])([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 97268Di-tert-butyl azodicarboxylateHCID 59593434(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide

Product 1

HCID 59593433HCID 59593433, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl-N-tert-butoxycarbonyliminocarbamate (2.44 g, 10.61 mmol) in THF (17.25 mL) at 0° C. was added n-tributylphosphine (2.15 g, 2.64 mL, 10.61 mmol) dropwise, the cooling bath was removed and the reaction mixture stirred at RT for 20 min. The reaction mixture was then cooled to 0° C. and a solution of (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide (1.15 g, 2.65 mmol) in THF (17.25 mL) was added slowly, the cooling bath removed and the reaction mixture stirred at RT for 45 min. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organics were washed with water (2×), brine, dried over MgSO4 and evaporated to dryness. Purification by silica gel chromatography (1-10% EtOAc in hexane) afforded (R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one (1.1 g, 96%) as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 7.81 (dd, J=1.5, 7.7 Hz, 2H), 7.72-7.66 (m, 4H), 7.51-7.36 (m, 8H), 7.15 (m, 1H), 4.51 (dd, J=8.1, 9.2 Hz, 1H), 3.72-3.59 (m, 2H), 2.26-2.21 (m, 1H), 2.03-1.98 (m, 1H) and 1.06 (s, 9H) ppm. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=416.7; tR=2.40 min.

Workup

  1. customthe cooling bath was removed
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customthe cooling bath removed
  4. stirringthe reaction mixture stirred at RT for 45 min
  5. additionThe reaction mixture was poured into water
  6. extractionextracted with EtOAc (3×)
  7. washThe combined organics were washed with water (2×), brine
  8. dry with materialdried over MgSO4
  9. customevaporated to dryness
  10. customPurification by silica gel chromatography (1-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-4eb1e1c8e9c34ed185d9fc9e25737ccf
Source dataset
uspto-grants-2010_12
Patent number
US07846954B2

Reaction notes

Loading…