HCID 11951635, compound → HCID 11568746, compound

HRID 2246905Notes

Reaction equation

HRID 2246905 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:8][NH:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.COC(C)(C)C>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C@@H:10]2[C@@H:9]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:8][NH:7][C@H:6]([CH2:4][OH:3])[CH2:11]2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 11951635HCID 11951635, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11568746HCID 11568746, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a stirred solution of 0.10 g of (2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-2-carboxylic acid ethyl ester in 10 ml of tetrahydrofuran are added 17.0 mg of lithium aluminium hydride at 0° C. The reaction mixture is stirred for 1 hour at this temperature, diluted with tert-butyl methyl ether and quenched by addition of 2.0 ml of aqueous saturated sodium sulfate solution. The mixture is allowed to warm to room temperature, filtered and dried over sodium sulfate. The solvent is concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound.

Workup

  1. customquenched by addition of 2.0 ml of aqueous saturated sodium sulfate solution
  2. filtrationfiltered
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent is concentrated under reduced pressure
  5. customthe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-35ddd79b997c4233a5dabaa0d99d51d7
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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