Methanol → HCID 89524677, compound

HRID 1621002Notes

Reaction equation

HRID 1621002 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][N:18]3C(OC(C)(C)C)=O)=[O:16])[CH:14]=[CH:13][NH:12][CH:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+].[OH2:32].[CH3:33][OH:34]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:15]([OH:16])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:14][CH2:13][N:12]([C:33]([O:34][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:32])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 131731658HCID 131731658, compound

Product 1

HCID 89524677HCID 89524677, compound

Conditions

Temperature
25 °C

Procedure

To a solution of Example 140B (500 mg, 1.11 mmol) in dry MeOH (5 mL) was added NaBH4 (84 mg, 2.22 mmol) at 0° C. The mixture was stirred at 25° C. for 1 hour and water (10 mL) was added slowly. The aqueous phase was separated and extracted with dichloromethane (2×20 mL). The combined organic phases were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=1/1) to give Example 140C.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with dichloromethane (2×20 mL)
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=1/1)
  8. customto give Example 140C

Sources & evidence

ORD record
ord-1618a8290b8a40b2946650ed9caf2147
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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