Dabco → HCID 72485645, compound

HRID 1593659Notes

Reaction equation

HRID 1593659 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][O:30][C:31](C#N)=[O:32].C1N2C[CH2:42][N:37](CC2)C1>>[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15]([C:42]#[N:37])([O:18][C:31]([O:30][CH3:29])=[O:32])[CH:14]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH:13]2[O:27][C:31]([O:30][CH3:29])=[O:32])[CH2:11][C:10]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 9237DabcoHCID 28660Carbonocyanidic acid, methyl esterHCID 72485635HCID 72485635, compound

Product 1

HCID 72485645HCID 72485645, compoundYield 874.9%

Procedure

To a mixture of rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-5-hydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (3) (95 mg, 0.235 mmol) and methylcyanoformate (169 μl, 2.115 mmol) was added at room temperature DABCO (3 mg, 0.023 mmol). The mixture was stirred at room temperature for 14 h and then concentrated under reduced pressure. The residue was triturated with Et2O, filtered and the solvent was evaporated under reduced pressure to give rac-(4R,5S,6S,7S)-1-benzyloxy-7-cyano-6-tert-butyldimethylsilyloxy-5,7-bis(methoxycarbonyloxy)-1-azaspiro[3.5]nona-8-ene-2-one (9) as a brown oil (110 mg, 86%), was used in the next reaction without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was triturated with Et2O
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-377ff184d58b49d8bdcaa6fca5552e04
Source dataset
uspto-grants-2007_11
Patent number
US07297788B2

Reaction notes

Loading…