Sodium borohydride → HCID 57969096, compound

HRID 1483653Notes

Reaction equation

HRID 1483653 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([B:18]3[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]3)=[C:14]([CH:27]=[O:28])[CH:13]=2)=[CH:7][C:6]=1[O:29][CH3:30])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([B:18]3[O:22][C:21]([CH3:23])([CH3:24])[C:20]([CH3:26])([CH3:25])[O:19]3)=[C:14]([CH2:27][OH:28])[CH:13]=2)=[CH:7][C:6]=1[O:29][CH3:30])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57969217HCID 57969217, compound

Product 1

HCID 57969096HCID 57969096, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 8 (3.22 g, 7.55 mmol) in methanol (40 mL) was added sodium borohydride (0.373 g, 9.82 mmol) at 0° C. The resulting mixture was stirred at rt for 30 min. The solvent was removed under reduced pressure, diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layer was dried over Na2SO4, and concentrated under reduced pressure to give crude product and used in the next step without further purification. 1H NMR 400 MHz (CDCl3) δ: 7.91 (d, J=8.2 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.01 (s, 1H), 6.98 (d, J=8.2 Hz, 1H), 6.60 (s, 1H), 6.67 (d, J=8.6 Hz, 1H), 4.65 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 3.81 (s, 3H), 1.42 (s, 12H), 1.20 (t, J=7.0 Hz, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give crude product
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-4b365f849ab1410e996acdc263ceb780
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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