Sodium Chloride → HCID 53754486, compound

HRID 428309Notes

Reaction equation

HRID 428309 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([C@H:22]([C@@H:24]([C@@H:26]([CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=1)[OH:25])[OH:23])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[Na+]>CO.[Pd]>[CH2:1]([O:8][CH2:9][C@H:10]([C@H:22]([C@@H:24]([C@@H:26]([CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[O:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([NH2:35])=[CH:33][CH:34]=1)[OH:25])[OH:23])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 54111386HCID 54111386, compound

Product 1

HCID 53754486HCID 53754486, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,6-di-O-benzyl-2,5-di-O-(4-nitrobenzyl)-D-mannitol (64 mg, 0.1 mmol) prepared in example 74 in MeOH was added 5% palladium on charcoal (40 mg) and sodium borohydride (114 mg, 3.0 mmol). The reaction mixture was stirred at room temperature for 2 h. Saturated sodium chloride (2 mL) was added and stirring was continued for 5 h. The mixture was extracted with EtOAc, dried over magnesium sulfate and concentrated in vacuo to yield (44 mg, 85%) after purification by flash chromatography.

Workup

  1. stirringstirring
  2. waitwas continued for 5 h
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield (44 mg, 85%)
  7. customafter purification by flash chromatography

Sources & evidence

ORD record
ord-7f5003fda31c430998bffc7e426d3d4f
Source dataset
uspto-grants-2001_11
Patent number
US06313177B1

Reaction notes

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