Sodium borohydride → HCID 71117151, compound

HRID 1410305Notes

Reaction equation

HRID 1410305 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@@H:22]1[O:27][C@H:26]([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[C@@H:25]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:24]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@H:23]1[O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)C=C.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:11][C:9]1[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]([C@H:22]2[C@H:23]([O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C@@H:24]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C@H:25]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@@H:26]([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[O:27]2)=[C:5]([OH:4])[CH:10]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86728590HCID 86728590, compound

Product 1

HCID 71117151HCID 71117151, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(((2R,3R,4R,5S,6S)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methoxy)pentan-1-ol (29, 479 mg, 0.584 mmol) from Step 2 in tetrahydrofuran (6 mL) were added sodium borohydride (177 mg, 4.668 mmol) and tetrakis(triphenylphosphine)palladium (67.5 mg, 0.058 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and quenched with saturated ammonium chloride, extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. Flash chromatography on a Biotage® apparatus (silica gel, 10 to 50% tetrahydrofuran in hexanes gradient) gave the title compound (30, 459 mg, 0.58 mmol, 100%) as colorless oil.

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-27ecc34d43224a248c6deaf21c4cce8d
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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