HCID 67022041, compound → HCID 67021969, compound

HRID 2094593Notes

Reaction equation

HRID 2094593 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][C@H:12]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[N:11]1[C:24]1[N:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=2)[N:27]=[C:26]([N:39]2[CH:44]3[CH2:45][CH2:46][CH:40]2[CH2:41][O:42][CH2:43]3)[N:25]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>[Pd].O1CCCC1>[CH:40]12[N:39]([C:26]3[N:25]=[C:24]([N:11]4[C@@H:12]([CH2:15][O:16][Si:17]([C:20]([CH3:22])([CH3:23])[CH3:21])([CH3:19])[CH3:18])[CH2:13][CH2:14][C@H:10]4[CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[N:29]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=4)[N:27]=3)[CH:44]([CH2:45][CH2:46]1)[CH2:43][O:42][CH2:41]2

Participants

5

Reactant 2

HCID 67022041HCID 67022041, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67021969HCID 67021969, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of palladium on charcoal (10%, 50 mg) and 8-(4-((2S,5R)-2,5-bis((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (0.55 g, 1.2 mmol) in tetrahydrofuran (20 mL) was stirred under a balloon of hydrogen overnight. The mixture was filtered through a pad of Celite™ diatomaceous earth and concentrated under reduced pressure to provide the title compound as a tan foam (0.42 g, 80%). MS (ES+)=642.4 (M+H)+

Workup

  1. filtrationThe mixture was filtered through a pad of Celite™ diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7aca796df2a74fd5932676609070f63f
Source dataset
uspto-grants-2013_05
Patent number
US08445486B2

Reaction notes

Loading…