Sodium borohydride → HCID 70642497, compound

HRID 660374Notes

Reaction equation

HRID 660374 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C@H:16]([CH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][N:27]2[CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:23][CH:22]=1)[CH:17]([CH3:19])[CH3:18])[C:10](OCC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:15][C@H:16]([CH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][N:27]2[CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:23][CH:22]=1)[CH:17]([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70642498HCID 70642498, compound

Product 1

HCID 70642497HCID 70642497, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (2S,4S)-ethyl 2-(tert-butoxycarbonylamino)-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexanoate (7.2 g, 15.2 mmol) in EtOH (100 mL) was added NaBH4 (5.0 g, 131 mmol) in portions such that the temperature remained lower than 40° C. The mixture was stirred at rt for 12 h. TLC showed the starting material had been consumed. The solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, and evaporated to produce tert-butyl (2S,4S)-1-hydroxy-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexan-2-ylcarbamate (5.8 g, 88%). MS: 434 (M++1)

Workup

  1. customremained lower than 40° C
  2. customhad been consumed
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between water and EtOAc
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-319a35fea1394c48bd5f03c6a3e0dc1e
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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