Sodium triacetoxyborohydride → HCID 9826057, compound

HRID 413286Notes

Reaction equation

HRID 413286 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([CH:12]=[O:13])[C:9]([CH2:14][N:15]3[CH2:20][CH2:19][C:18]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)=[N:8]2)=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([CH2:12][OH:13])[C:9]([CH2:14][N:15]3[CH2:16][CH2:17][C:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:19][CH2:20]3)=[N:8]2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 9912542HCID 9912542, compound

Product 1

HCID 9826057HCID 9826057, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

The product of Example 15 (0.05 g) was dissolved in dichloromethane (5 ml) and sodium triacetoxyborohydride (0.068 g) added. After 20 hours at room temperature, brine and dichloromethane were added, the organic phase was separated, dried and the solvent removed by evaporation to give a residue. Trituration under ether gave the product as a solid (0.028 g), m.p. 104-105° C.

Workup

  1. customthe organic phase was separated
  2. customdried
  3. customthe solvent removed by evaporation
  4. customto give a residue

Sources & evidence

ORD record
ord-ead7676ff1814b0e9826da1346be3239
Source dataset
uspto-grants-2003_05
Patent number
US06566376B1

Reaction notes

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