Sodium borohydride → HCID 86718381, compound

HRID 1518769Notes

Reaction equation

HRID 1518769 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C@H:15]([OH:21])[C:16](OCC)=[O:17])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.CO>[OH:21][C@H:15]([CH2:16][OH:17])[C@H:14]([NH:13][C:11](=[O:12])[O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86718382HCID 86718382, compound

Product 1

HCID 86718381HCID 86718381, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (1.06 g, 28 mmol, 3.0 equiv) was added to a solution of 2.21.1a (3.5 g, 9.4 mmol, 1.0 equiv) in THF (10.0 mL) and MeOH (30 mL) at 0° C. The resulting mixture was stirred at room temperature for 1 hour, after which, another 0.3 g of NaBH4 (300 mg, 7.8 mmol, 0.8 equiv) was added. After stirring at room temperature for 30 minutes, the solvent was removed under vacuum. The residue was dissolved in EtOAc and saturated aqueous NaHCO3 solution was added. The phases were separated and the organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude material was used in the next step with no further purification. MS m/z (M+Na): 354

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. additionsaturated aqueous NaHCO3 solution was added
  5. customThe phases were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude material was used in the next step with no further purification

Sources & evidence

ORD record
ord-d1d70ca8b71c4636b7678ac58137600e
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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