Sodium borohydride → HCID 66993325, compound

HRID 1637888Notes

Reaction equation

HRID 1637888 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. MP: 206° C.

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-f5dcceb440c2476cb84d5d80110b886d
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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