Methanol → HCID 89533788, compound

HRID 920275Notes

Reaction equation

HRID 920275 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.CO.[BH4-].[Na+]>C1COCC1>[OH:1][CH:2]1[C:11]2[CH:10]=[C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 18180286HCID 18180286, compound

Product 1

HCID 89533788HCID 89533788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound of Formula 39-1 (740 mg, 2.83 mmol) in THF (5 mL)/MeOH (5 mL) was added sodium borohydride (107 mg, 2.83 mmol) while cooled at 0° C. The solution was stirred for 1 hour and concentrated to volume in vacuo. The residue was diluted with EtOAc (40 mL) and washed with sat'd sodium bicarbonate (2×10 mL) and brine (10 mL). Organics were dried over sodium sulfate, filtered, and concentrated in vacuo to yield the compound of Formula 39-2 as a solid.

Workup

  1. concentrationconcentrated to volume in vacuo
  2. additionThe residue was diluted with EtOAc (40 mL)
  3. washwashed with sat'd sodium bicarbonate (2×10 mL) and brine (10 mL)
  4. dry with materialOrganics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e618bc7455048d4b71644a03a0c7f4f
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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