HCID 86690060, compound → HCID 86690061, compound

HRID 539410Notes

Reaction equation

HRID 539410 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2([C:33](=[O:42])[NH:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([C:17]2([C:33](=[O:42])[NH:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)(=[O:15])=[O:16])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86690060HCID 86690060, compound

Product 1

HCID 86690061HCID 86690061, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-((4-Phenoxyphenyl)sulfonyl)-4-(((tetrahydro-2H-pyran-2-yl)oxy)carbamoyl)piperidine was synthesized as shown in FIG. 13. A 200 ml RBF equipped with magnetic stir bar was charged with the 1.5 g of benzyl 4-((4-phenoxyphenyl)sulfonyl)-4-(((tetrahydro-2H-pyran-2-yl)oxy)carbamoyl)piperidine-1-carboxylate compound and 100 mg wet Degussa 5% Palladium on Carbon in 45 ml Methanol. The reaction mixture was purged with Argon for 5 minutes. Hydrogen was then bubbled over the solution for 1 hr. MS analysis (direct infusion) at this point indicated that the reaction was complete. The crude was filtered through Celite and the Celite was washed with 40 ml additional methanol. The methanol solution was concentrated in vacuo to 1.2 g white solid that was vacuum dried for 4 hours to yield 1.1 g product that was used in Step 5. HRMS(observed) M H=451.1737 g/mol.

Workup

  1. customA 200 ml RBF equipped with magnetic stir bar
  2. customThe reaction mixture was purged with Argon for 5 minutes
  3. customHydrogen was then bubbled over the solution for 1 hr
  4. filtrationThe crude was filtered through Celite
  5. washthe Celite was washed with 40 ml additional methanol
  6. concentrationThe methanol solution was concentrated in vacuo to 1.2 g white solid
  7. customdried for 4 hours

Sources & evidence

ORD record
ord-0cea2a26e9d346f3bd93a09426abe3a3
Source dataset
uspto-grants-2014_10
Patent number
US08871189B2

Reaction notes

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