(2R,3R,4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran → (2R,3R,4S)-6-amino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran

HRID 29032Notes

Reaction equation

HRID 29032 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@:11]([CH:14]([O:17][CH3:18])[O:15][CH3:16])([CH3:13])[C@H:10]([OH:19])[C@@H:9]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][C:21]3=[S:29])[C:8]=2[CH:30]=1)([O-])=O.[H][H]>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@:11]([CH:14]([O:17][CH3:18])[O:15][CH3:16])([CH3:13])[C@H:10]([OH:19])[C@@H:9]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][C:21]3=[S:29])[C:8]=2[CH:30]=1

Participants

5

Reactant 2

HCID 86612092(2R,3R,4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyranHCID 178418361HCID 178418361, compound

Product 1

HCID 86612091(2R,3R,4S)-6-amino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyranYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 935NickelSolvent

Procedure

200 mg (0.46 mmol) of the compound obtained in Example 1 was dissolved in 10 ml of methanol, to which 100 mg of Raney-Ni was added. Reaction was continued for 14 hours at room temperature with 3 atmospheric pressure of hydrogen gas. The reaction solution was filtered to eliminate Ni, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), to give 177 mg (yield: 96%) of the target compound.

Workup

  1. additionwas added
  2. customReaction
  3. filtrationThe reaction solution was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-914079a0b0734b50a09c2760497d7233
Source dataset
uspto-grants-2008_09
Patent number
US07420060B2

Reaction notes

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