3,4-dihydro-2H-pyran → HCID 178499316, compound

HRID 1694496Notes

Reaction equation

HRID 1694496 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])[C@H:20]1[CH2:21][CH2:22][C@H:23]([O:26][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[CH2:24][CH2:25]1)=[O:4]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 178499317HCID 178499317, compound

Product 1

HCID 178499316HCID 178499316, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (140 mg, 0.37 mmol) in DCM (4 mL) p-toluenesulfonic acid monohydrate (6 mg) and 3,4-dihydro-2H-pyran (38 μl, 0.42 mmol) were added at room temperature. After stirring for 1 h and 10 min saturated NaHCO3 was added. It was extracted with DCM, washed with brine, dried (MgSO4) and evaporated. The crude material was chromatographed over silica gel (prewashed with Et3N) (hexane:EtOAc—9:1 as eluent) yielding pure 3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (83 mg, 48%).

Workup

  1. additionwas added
  2. extractionIt was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material was chromatographed over silica gel (prewashed with Et3N) (hexane:EtOAc—9:1 as eluent)

Sources & evidence

ORD record
ord-564a9317ed864280bf98fae01d44bebe
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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