HCID 67022116, compound → HCID 67022191, compound

HRID 1665573Notes

Reaction equation

HRID 1665573 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[CH2:45][CH:44]3[O:46][CH:41]([CH2:42][CH2:43]3)[CH2:40]2)[N:25]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>[Pd].O1CCCC1>[CH:41]12[O:46][CH:44]([CH2:43][CH2:42]1)[CH2:45][N:39]([C:26]1[N:25]=[C:24]([N:11]3[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]3[CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[N:29]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=3)[N:27]=1)[CH2:40]2

Participants

5

Reactant 2

HCID 67022116HCID 67022116, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67022191HCID 67022191, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of palladium on charcoal (10%, 100 mg) and crude 3-(4-((2S,5R)-2,5-bis((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane (3.4 mmol maximum) in tetrahydrofuran (30 mL) was shaken for 8 hours under 50 psi of hydrogen. The mixture was filtered through a pad of Celite™ diatomaceous earth and concentrated under reduced pressure to provide the title compound as an orange foam. 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-af10fb416b99406f9f0498e0d1f9fb0b
Source dataset
uspto-grants-2011_10
Patent number
US08039469B2

Reaction notes

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