Sodium borohydride → HCID 10225227, compound

HRID 1830821Notes

Reaction equation

HRID 1830821 reaction equation
[NH2:1][C:2]1[C:28]([CH3:29])=[C:27]([CH3:30])[C:5]([O:6][CH2:7][C:8]([N:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:20])[CH2:14][CH2:13]2)[CH3:11])=[O:9])=[C:4]([CH3:31])[C:3]=1[CH3:32].[BH4-].[Na+]>CO>[NH2:1][C:2]1[C:3]([CH3:32])=[C:4]([CH3:31])[C:5]([O:6][CH2:7][C:8]([N:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([OH:20])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:14][CH2:13]2)[CH3:11])=[O:9])=[C:27]([CH3:30])[C:28]=1[CH3:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10137992HCID 10137992, compound

Product 1

HCID 10225227HCID 10225227, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture solution of the compound (10) obtained in the Example 10 in methanol was added 1.0 equivalent of sodium borohydride at 0° C., and the mixture was stirred for 1.5 hours at the room temperature. After the reaction, the solvent was removed under reduced pressure, and the resulting residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.) column chromatography (dichloromethane : methanol =20:1) to give the above-mentioned compound (11) in the yield of 58%.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed under reduced pressure
  3. customthe resulting residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.) column chromatography (dichloromethane : methanol =20:1)

Sources & evidence

ORD record
ord-6981cc04d3f449029d917ce6b9a81a1b
Source dataset
uspto-grants-2006_06
Patent number
US07067533B2

Reaction notes

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