Methanol → HCID 58189016, compound

HRID 1423139Notes

Reaction equation

HRID 1423139 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:35])[CH2:29][C:30](OCC)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CO>C1COCC1>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:35])[CH2:29][CH2:30][OH:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86652001HCID 86652001, compound

Product 1

HCID 58189016HCID 58189016, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ((S)-ethyl 3-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-oxopropanoate (96 mg, 0.20 mmol) and sodium borohydride (30 mg, 0.80 mmol) in THF (4 mL) was brought to reflux and MeOH (242 μL, 6.0 mmol) added drop-wise over a 1 h period. The reaction mixture was allowed to heat at reflux for an additional 16 h and then quenched with a few drops of a 1 N HCl solution. The reaction was partitioned between EtOAc (10 mL) and a saturated aqueous solution of NaHCO3 (10 mL). The organic extract was further washed with brine then dried over MgSO4, filtered, and evaporated to an oil that was purified by silica gel flash chromatography with EtOAc as eluant to afford the title compound as an oil (51 mg, 58%). LC/MS (Method A) 4.34 min, [M+1]+ 439.

Workup

  1. temperatureto reflux
  2. temperatureto heat
  3. temperatureat reflux for an additional 16 h
  4. customquenched with a few drops of a 1 N HCl solution
  5. customThe reaction was partitioned between EtOAc (10 mL)
  6. extractionThe organic extract
  7. washwas further washed with brine
  8. dry with materialthen dried over MgSO4
  9. filtrationfiltered
  10. customevaporated to an oil that
  11. customwas purified by silica gel flash chromatography with EtOAc as eluant

Sources & evidence

ORD record
ord-6a492be4d062494ea63fca72c6546db0
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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