Sodium borohydride → HCID 178471782, compound

HRID 505307Notes

Reaction equation

HRID 505307 reaction equation
[CH2:1]([N:3]([CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]1)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[CH:14]=[O:15])[CH3:2].[BH4-].[Na+]>CCO>[CH2:1]([N:3]([CH2:16][C@H:17]1[CH2:18][CH2:19][C@H:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:21][CH2:22]1)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:5]=1[CH2:14][OH:15])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178471781HCID 178471781, compound

Product 1

HCID 178471782HCID 178471782, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl [trans-4-({ethyl[2-formyl-4-(trifluoromethyl)phenyl]amino}methyl)cyclohexyl]acetate (Step A; 153 mg; 0.38 mmol) in EtOH (1 mL) was added sodium borohydride (7.3 mg; 0.19 mmol). The reaction stirred at room temperature for 1 h and was concentrated in vacuo. The residue was redissolved in EtOAc (10 mL) and washed with sat. NH4Cl (10 mL). The aqueous layer was re-extracted with EtOAc (2×10 mL) and the combined organic layers were washed with H2O and brine (10 mL each), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford ethyl [trans-4-({ethyl[2-(hydroxymethyl)-4-(trifluoromethyl)phenyl]amino}methyl)cyclohexyl]acetate as a yellow oil. LCMS=402.2 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.56-7.54 (m, 2 H), 7.29-7.26 (m, 1 H), 4.85 (s, 2 H), 4.13 (q, J=7.1 Hz, 2 H), 3.10-3.02 (m, 2 H), 2.91-2.85 (m, 2 H), 2.17 (d, J=6.9 Hz, 2 H), 1.84-1.70 (m, 4 H), 1.57-1.44 (m, 2 H), 1.39-1.31 (m, 1 H), 1.26 (t, J=7.1 Hz, 3 H), 1.08-1.04 (m, 3 H), 1.01-0.93 (m, 3 H).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was redissolved in EtOAc (10 mL)
  3. washwashed with sat. NH4Cl (10 mL)
  4. extractionThe aqueous layer was re-extracted with EtOAc (2×10 mL)
  5. washthe combined organic layers were washed with H2O and brine (10 mL each)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-31c429525516471685266f55a912382d
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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