Sodium borohydride → HCID 66993325, compound

HRID 1953526Notes

Reaction equation

HRID 1953526 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][CH:27]=3)=[CH:4][C:3]=2[O:2]1.[BH4-].[Na+]>CO.C(Cl)Cl>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]3[CH:27]=[CH:28][C:29]([CH2:32][OH:33])=[CH:30][CH:31]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 87228647HCID 87228647, compound

Product 1

HCID 66993325HCID 66993325, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

This product was prepared by stirring a solution of Example 23 (0.3 g, 0.66 mmol) in 40 mL of MeOH with NaBH4 (0.1 g, 4 equiv.) at rt for two hours. Evaporation of the solvent gave a residue which was dissolved in DCM (100 mL) and washed twice with water (50 mL). Extraction with DCM, drying over MgSO4 and evaporation in vacuo gave the title compound (0.2 g, 67%) as white crystals after recrystallization from EtOH.

Workup

  1. customThis product was prepared
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. washwashed twice with water (50 mL)
  5. extractionExtraction with DCM
  6. dry with materialdrying over MgSO4 and evaporation in vacuo

Sources & evidence

ORD record
ord-1c3cd7b243864bbfa8d925013a1b9574
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

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