D-Psicose → HCID 86709520, compound

HRID 1848528Notes

Reaction equation

HRID 1848528 reaction equation
C([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[N:14]([C:17]3[CH2:21]C[C:19](=[O:22])[C:18]=3[CH3:23])[CH2:13][CH2:12]2)[CH:10]([OH:26])[CH2:9]1)C1C=CC=CC=1.C(O[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(C)(C)C.[OH:39]CC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[OH:26][CH:10]1[CH2:9][N:8]([C:32]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:38])[CH2:25][CH2:24][C:11]21[C:15](=[O:16])[N:14]([C:17]1[CH2:21][O:39][C:19](=[O:22])[C:18]=1[CH3:23])[CH2:13][CH2:12]2

Participants

6

Reactant 3

HCID 441036D-PsicoseHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 86709521HCID 86709521, compound

Product 1

HCID 86709520HCID 86709520, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-benzyl-6-hydroxy-2-(2-methyl-3-oxocyclopent-1-en-1-yl)-2,8-diazaspiro[4.5]decan-1-one (CIS) (10 g, 28.2 mmol) and di-tert-butylcarbonate (7.21 ml, 31.0 mmol) in methanol (50 ml) was added palladium on carbon (1.501 g, 1.411 mmol), and the resulting mixture was subjected to hydrogenation at 45 Psi at rt over the weekend. The suspension was filtered through CELITE® under nitrogen, the filtrate was concentrated and the residue was purified on silica gel using ethyl acetate/hexane as eluting solvents to give the title compound. LC/MS: (M+1)+: 367.17.

Workup

  1. filtrationThe suspension was filtered through CELITE® under nitrogen
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified on silica gel
  4. washas eluting solvents

Sources & evidence

ORD record
ord-fd76bb98938d46f69eae232833e12f81
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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