Aluminium lithium hydride → HCID 52913265, compound

HRID 1944098Notes

Reaction equation

HRID 1944098 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH2:50]O)[CH2:48][OH:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH2:46][CH3:47])=[CH:43][CH:44]=3)[CH:32]=2)[O:11][C:10]1([CH2:48][OH:49])[CH3:50])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 52914724HCID 52914724, compound

Product 1

HCID 52913265HCID 52913265, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of bis-tosylate of {(3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol (250 mg, 0.20 mmol) in dry THF (15 mL) was added lithium aluminum hydride (40 mg, 0.80 mmol) at 0° C. and heated at 70° C. for 16 hour. The excess lithium aluminum hydride was quenched with saturated aqueous sodium sulfate solution and filtered through celite bed. The filtrate was concentrated and purified by using silica gel column chromatography (30% ethyl acetate in hexane) to furnish 150 mg of {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-methyl-tetrahydro-pyran-2-yl}-methanol.

Workup

  1. customThe excess lithium aluminum hydride was quenched with saturated aqueous sodium sulfate solution
  2. filtrationfiltered through celite bed
  3. concentrationThe filtrate was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-3bd1ce183d8840958d9b726749b1ccfc
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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