Sodium borohydride → HCID 67287563, compound

HRID 46206Notes

Reaction equation

HRID 46206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[C:47]([C:49]1[N:50]=[N:51][C:52]([O:55][CH2:56][CH3:57])=[CH:53][CH:54]=1)=[O:48].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[O:9]2)=[CH:4][C:3]=1[CH:47]([C:49]1[N:50]=[N:51][C:52]([O:55][CH2:56][CH3:57])=[CH:53][CH:54]=1)[OH:48]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67287362(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)(6-ethoxypyridazin-3-yl)methanone

Product 1

HCID 67287563HCID 67287563, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)(6-ethoxypyridazin-3-yl)methanone (970 mg; 1.24 mmol) in MeOH (20 mL) was added NaBH4 (93.5 mg; 2.47 mmol) at 0° C., then stirred for 3 h at room temperature. The reaction was quenched with 2N HCl, extracted with ethyl acetate (3×50 mL) and washed with brine. The organic layer was dried over MgSO4 and the solvents were evaporated under a vacuum. The crude mixture was further purified by flash column chromatography (Biotage SP1™) (eluent: hexane/EtOAc mixture (40/60; v/v)) to obtain 907 mg (1.15 mmol; 93%) of the title compound as colorless oil.

Workup

  1. customThe reaction was quenched with 2N HCl
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvents were evaporated under a vacuum
  6. customThe crude mixture was further purified by flash column chromatography (Biotage SP1™) (eluent: hexane/EtOAc mixture (40/60; v/v))

Sources & evidence

ORD record
ord-93cf076b82f84a2e9ac36eeb03dc7fc5
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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