(Trimethylsilyl)imidazole → HCID 72485669, compound

HRID 1593656Notes

Reaction equation

HRID 1593656 reaction equation
[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15](=[O:18])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:13]2[OH:27])[CH2:11][C:10]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][Si:30]([CH3:37])([CH3:36])N1C=CN=C1>>[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15](=[O:18])[CH:14]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH:13]2[O:27][Si:30]([CH3:37])([CH3:36])[CH3:29])[CH2:11][C:10]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 28925(Trimethylsilyl)imidazoleHCID 72485635HCID 72485635, compound

Product 1

HCID 72485669HCID 72485669, compoundYield 65.3%

Procedure

A solution of rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-5-hydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (3) (130 mg, 0.322 mmol) in 1-trimethylsilylimidazole (0.5 ml, 3.220 mmol) was stirred at room temperature for 16 h. The reaction was quenched with Na2PO4 0.1 M buffer (2 ml) and the mixture extracted with AcOEt (3×4 ml). The combined extracts were washed with saturated aqueous CuSO4 solution (1×8 ml) and brine (2×8 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-AcOEt, 5:1) to give rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-5-trimethylsilyloxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (6) as a white solid (100 mg, 65%).

Workup

  1. customThe reaction was quenched with Na2PO4 0.1 M buffer (2 ml)
  2. extractionthe mixture extracted with AcOEt (3×4 ml)
  3. washThe combined extracts were washed with saturated aqueous CuSO4 solution (1×8 ml) and brine (2×8 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-AcOEt, 5:1)

Sources & evidence

ORD record
ord-c85e3e368f3b46aabc758783c47695ee
Source dataset
uspto-grants-2007_11
Patent number
US07297788B2

Reaction notes

Loading…