(S)-2'-amino-3-(3,6-dihydro-2H-pyran-4-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol → (S)-2'-amino-3-(tetrahydro-2H-pyran-4-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

HRID 335737Notes

Reaction equation

HRID 335737 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH2:21][CH2:22][O:23][CH2:24][CH:25]=4)[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([OH:26])=[CH:10][CH:11]=3)[N:6]=1>[Pd].CO>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([OH:26])=[CH:10][CH:11]=3)[N:6]=1

Participants

4

Reactant 1

HCID 67241212(S)-2'-amino-3-(3,6-dihydro-2H-pyran-4-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

Product 1

HCID 67383563(S)-2'-amino-3-(tetrahydro-2H-pyran-4-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 25-mL flask was charged with (S)-2′-amino-3-(3,6-dihydro-2H-pyran-4-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol (211 mg, 0.601 mmol) and MeOH (75070 μL). The mixture was sonicated for 1 min to give an opaque mixture. Palladium on carbon (63.9 mg, 0.060 mmol) was added, and H2 (g) was bubbled through the mixture for 1 min. The mixture was stirred further under a balloon of H2 (g) for 60 hours. The mixture was filtered through celite with the aid of methanol. The filtrate was evaporated, and the residue was chromatographed on a 40-g Redi-Sep column with 0-100% of a 90:10:1 mix of DCM/MeOH/NH4OH to give (S)-2′-amino-3-(tetrahydro-2H-pyran-4-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol as an off-white solid.

Workup

  1. customThe mixture was sonicated for 1 min
  2. customto give an opaque mixture
  3. customH2 (g) was bubbled through the mixture for 1 min
  4. filtrationThe mixture was filtered through celite with the aid of methanol
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed on a 40-g Redi-Sep column with 0-100% of a 90:10:1
  7. additionmix of DCM/MeOH/NH4OH

Sources & evidence

ORD record
ord-e38405e7b7a1481aa9e2d4fa1636396e
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…