Sodium borohydride → HCID 56602660, compound

HRID 1260497Notes

Reaction equation

HRID 1260497 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:32][CH2:31][C:14]2([C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[C:13](=[O:33])[CH2:12]1)(=[O:10])=[O:9].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:32][CH2:31][C:14]2([C:18](=[O:19])[N:17]([C:20]3[CH:21]=[CH:22][C:23]([O:26][C:27]([F:29])([F:30])[F:28])=[CH:24][CH:25]=3)[CH2:16][CH2:15]2)[CH:13]([OH:33])[CH2:12]1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58056620HCID 58056620, compound

Product 1

HCID 56602660HCID 56602660, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of rac-8-(2-chloro-benzenesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,6-dione (34 mg, 67.6 μmol) in methanol was added sodium borohydride (2.81 mg, 74.4 μmol). The reaction mixture was stirred at room temperature for 6 h. The reaction mixture was quenched with 1N NaOH and diluted with further 1N NaOH and ethyl acetate. The organic layer was separated washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash column chromatography to give the title compound as an off white solid (5 mg, 15%) MS (ESI): 505.1 (MH+)

Workup

  1. customThe reaction mixture was quenched with 1N NaOH
  2. additiondiluted with further 1N NaOH and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude residue which
  9. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f85d9ca2c6da40d0b2fa8671bc82e369
Source dataset
uspto-grants-2013_06
Patent number
US08470843B2

Reaction notes

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