HCID 88191236, compound → HCID 70172656, compound

HRID 2306204Notes

Reaction equation

HRID 2306204 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:10]1=S)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])[CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 88191236HCID 88191236, compound

Product 1

HCID 70172656HCID 70172656, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent3×

Procedure

(R)-3-(tert-Butoxycarbonylamino)-1-[7-(tert-butyldimethylsilyloxy) naphthalen-1-yl]-2-thioxopyrrolidine, as described above in Step G, (1.04 g, 2.19 mmol) was dissolved in EtOH (100 mL) and Raney Ni (5 g of a slurry in EtOH) was added. The mixture was stirred at ambient temperature for 18 hours, then an additional portion of Raney Ni (3 g of a slurry in EtOH) was added. After a further 4 hours stirring, the reaction mixture was filtered through a pad of celite, washing with EtOH. The filtrate was concentrated in vacuo to provide the desired product.

Workup

  1. stirringAfter a further 4 hours stirring
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. washwashing with EtOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-edf6ddce9ede4b1097775ee3aca0f889
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

Loading…