Lithium borohydride → HCID 9827956, compound

HRID 460642Notes

Reaction equation

HRID 460642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C@H:16]([OH:38])[CH2:17][O:18][C:19]3[C:27]4[CH:26]=[C:25]([C:28]5[O:29][C:30]([C:33](OCC)=[O:34])=[N:31][N:32]=5)[O:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C@H:16]([OH:38])[CH2:17][O:18][C:19]3[C:27]4[CH:26]=[C:25]([C:28]5[O:29][C:30]([CH2:33][OH:34])=[N:31][N:32]=5)[O:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69498066HCID 69498066, compound

Product 1

HCID 9827956HCID 9827956, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-(4-(3,4-Dichlorophenyl)piperidino)-1-(2-(5-ethoxycarbonyl-1,3,4-oxadiazol-2-yl)benzo(b)furan-4-yloxy)-2-propanol (1.3 g) obtained in Example 135 was dissolved in THF (20 ml) and lithium borohydride (60 mg) was added with stirring under ice-cooling. The mixture was stirred for 1 hr at room temperature, then poured into ice-water, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give yellow crystals (1.2 g). The crystals were purified by silica gel column chromatography (chloroform/methanol) to give the title compound (100 mg) as pale-yellow crystals, melting point 158–160° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hr at room temperature
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8f69114899949c0a5bc2efe42beff1c
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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