Dabco → HCID 72485643, compound

HRID 1593657Notes

Reaction equation

HRID 1593657 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.C[Si:30]([C:33]#N)([CH3:32])[CH3:31].C1N2C[CH2:42][N:37](CC2)C1>O>[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15]([C:42]#[N:37])([O:18][Si:20]([CH3:23])([CH3:22])[CH3:21])[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]([CH3:31])([CH3:32])[CH3:33])[CH2:11][C:10]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 82115Trimethylsilyl cyanideHCID 72485635HCID 72485635, compound

Product 1

HCID 72485643HCID 72485643, compoundYield 883.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (3) (200 mg, 0.496 mmol) and trimethylsilyl cyanide (607 μl, 4.460 mmol) at room temperature (cooled with water bath) was slowly added DABCO (6 mg, 0.050 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-6-tert-butyldimethylsilyloxy-7-cyano-5,7-bis(trimethylsilyloxy)-1-azaspiro[3.5]nona-8-ene-2-one (7) as a orange solid (254 mg, 89%).

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-5491710473ee412e90654ecc8c8d9cbb
Source dataset
uspto-grants-2007_11
Patent number
US07297788B2

Reaction notes

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