Ammonium Chloride → HCID 67182866, compound

HRID 2410437Notes

Reaction equation

HRID 2410437 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C@H:16]3[O:25][C@@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@@H:18]4[C@@H:17]3[CH2:26][C:27](OCC)=[O:28])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C@H:16]3[O:25][C@@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@@H:18]4[C@@H:17]3[CH2:26][CH2:27][OH:28])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 86700976ethyl {(3aR,5R,6R,6aR)-5-[2-(4'-chlorobiphenyl-4-yl)ethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}acetate

Product 1

HCID 67182866HCID 67182866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained from step h above (0.75 g) in tetrahydrofuran (15 mL), lithium aluminum hydride (0.096 g) was added at 0° C. The resulting mixture was stirred for 3 hours at same temperature, and a saturated solution of ammonium chloride was then added. The reaction mixture was then filtered through silica gel (100 to 200 mesh) and concentrated. Ethyl acetate and water were added to the resulting residue. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to afford the title compound (0.65 g).

Workup

  1. filtrationThe reaction mixture was then filtered through silica gel (100 to 200 mesh)
  2. concentrationconcentrated
  3. additionEthyl acetate and water were added to the resulting residue
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bee632fcebb04b6796176b3872b2d671
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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