Dabco → HCID 69241595, compound

HRID 1593658Notes

Reaction equation

HRID 1593658 reaction equation
[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15](=[O:18])[CH:14]([OH:19])[CH:13]2[OH:20])[CH2:11][C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si:23]([C:26]#N)([CH3:25])[CH3:24].C1N2C[CH2:35][N:30](CC2)C1>O>[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15]([C:35]#[N:30])([O:18][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]([O:19][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]2[O:20][Si:23]([CH3:24])([CH3:25])[CH3:26])[CH2:11][C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 82115Trimethylsilyl cyanideHCID 69177826HCID 69177826, compound

Product 1

HCID 69241595HCID 69241595, compoundYield 638.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of rac-(4R,5S,6S)-1-benzyloxy-5,6-dihydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (2) (44 mg, 0.152 mmol) and trimethylsilyl cyanide (186 μl, 1.368 mmol) at room temperature (cooled with water bath) was slowly added DABCO (2 mg, 0.015 mmol). The mixture was stirred at room temperature for 14 h and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-AcOEt, 5:1) to give rac-(4R,5S,6S,7S)-1-benzyloxy-7-cyano-5,6,7-tris(trimethylsilyloxy)-1-azaspiro[3.5]nona-8-ene-2-one (8) as a yellow solid (51 mg, 62%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane-AcOEt, 5:1)

Sources & evidence

ORD record
ord-f661754e6f714148b3a3ee7e40e82190
Source dataset
uspto-grants-2007_11
Patent number
US07297788B2

Reaction notes

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