Sodium Hydroxide → HCID 3011270, compound

HRID 428310Notes

Reaction equation

HRID 428310 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([C@H:21]([C@@H:23]([C@@H:25]([CH2:36][O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[OH:24])[OH:22])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH2:38]([O:37][CH2:36][C@H:25]([C@H:23]([C@@H:21]([C@@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1)[OH:22])[OH:24])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3011266HCID 3011266, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3011270HCID 3011270, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,6-di-O-benzyl-2,5-di-O-(4-cyanobenzyl)-D-mannitol (100 mg, 0.17 mmol) (prepared in example 4) and lithium aluminum hydride (32 mg, 0.85 mmol) was heated at reflux for 3 h in THF. After cooling at room temperature, the reaction was treated with 2N sodium hydroxide and stirring was continued for a period of 5 h. The mixture was extracted with EtOAc and the extract was dried over magnesium sulfate and concentrated in vacuo. After purification by flash chrlomatography eluting with 10% MeOH in methylene chloride, the title compound was obtained in 37% yield.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe extract was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customAfter purification by flash chrlomatography
  5. washeluting with 10% MeOH in methylene chloride

Sources & evidence

ORD record
ord-24b1311982c84eaeb931ac3c2532fc6c
Source dataset
uspto-grants-2001_11
Patent number
US06313177B1

Reaction notes

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