Hydrochloric Acid → HCID 67440386, compound

HRID 1664406Notes

Reaction equation

HRID 1664406 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH3:36])[C:10]1[N:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]3[O:29][C:28](C)(C)C(C)(C)[O:26]3)=[C:21](C=O)[CH:20]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13])(C)(C)C.[BH4-].[Na+].Cl>CO>[OH:26][B:25]1[C:22]2[CH:23]=[CH:24][C:19]([O:18][C:16]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([N:9]([CH2:8][CH2:7][OH:6])[CH3:36])[N:17]=3)=[CH:20][C:21]=2[CH2:28][O:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636446HCID 86636446, compound

Product 1

HCID 67440386HCID 67440386, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 11 (5.2 g, 9.7 mmol) in MeOH (anhydrous, 150 mL) was slowly added NaBH4 (2.2 g, 58 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 150 mL). The stirring was kept at room temperature overnight. Then the solution was slowly evaporated in vacuo. Purification was accomplished by reverse phase Biotage with 5%-100% MeOH/H2O gradient to afford 786 mg (25% yield) of the desired product as a white solid.

Workup

  1. customThen the solution was slowly evaporated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-f3418e4de54c4c399d39752c69fbbc80
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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