Sodium borohydride → HCID 118362101, compound

HRID 2279981Notes

Reaction equation

HRID 2279981 reaction equation
C([O:3][C:4](=O)[CH:5]([N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:6]([OH:16])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)C.[BH4-].[Na+]>CO>[OH:3][CH2:4][CH:5]([N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[C@H:6]([OH:16])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118362112HCID 118362112, compound

Product 1

HCID 118362101HCID 118362101, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

β-hydroxy-α-hydrazino ester (6B) (465 mg, 1.0 mmol) was added to 25 mL MeOH, then 3.0 eq of NaBH4 (114 mg, 3.0 mmol) was added every 15 min until the starting material was consumed as indicated by TLC. The reaction was quenched with saturated NH4Cl (aq.), extracted with EtOAc, and the combined extracts were washed with brine, dried over anhydrous Na2SO4, and the solvent was removed in vacuo. Purification by chromatography on silica gel to afford the desired product as a white solid (83%) (Kim et al., Tetrahedron 2010, 66, 3995).

Workup

  1. customwas consumed
  2. customThe reaction was quenched with saturated NH4Cl (aq.)
  3. extractionextracted with EtOAc
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customthe solvent was removed in vacuo
  7. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-ad76cf7a084d40ef830a1bc4f20e8d28
Source dataset
uspto-grants-2015_09
Patent number
US09133488B2

Reaction notes

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