Ethanol → HCID 56597289, compound

HRID 2036195Notes

Reaction equation

HRID 2036195 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][C:22]=1[O:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[OH:38]>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([C:27](=[O:38])[NH2:28])[CH:24]=[CH:23][C:22]=1[O:29][CH2:30][C:31]([OH:33])=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 66653934HCID 66653934, compound

Product 1

HCID 56597289HCID 56597289, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (±)-1-(5-cyano-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (141 mg, 0.30 mmol, 1.0 eq.) in EtOH (0.5 mL) and water (0.12 mL), hydrido(dimethylphosphinous acid-kP)[hydrogen bis(dimethylphosphinito-kP)]platinum(II) (26 mg, 0.06 mmol, 0.2 eq.) was added in one portion at r.t. The reaction mixture was stirred at 70° C. for 1 hour, then allow to cool to r.t. The product solution was then filtered through a short column containing a layer of Na2SO4 on top of a layer of SiO2 (each 1 cm deep), eluting with AcOEt (200 mL). The filtrate was concentrated in vacuo. To a solution of the residue in DMF (2 mL), 1M aq. NaOH (0.5 ml) was added. The resulting solution was stirred at r.t. for 6 hours. The mixture was neutralized with formic acid (0.5 mL), filtered, and purified by prep. HPLC (column: Waters X-Bridge, 19×50 mm, 5 um, UV/MS, acidic conditions) to give the desired acid as a white solid.

Workup

  1. temperatureto cool to r.t
  2. filtrationThe product solution was then filtered through a short column
  3. additioncontaining a layer of Na2SO4 on top of a layer of SiO2 (each 1 cm deep),
  4. washeluting with AcOEt (200 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionTo a solution of the residue in DMF (2 mL), 1M aq. NaOH (0.5 ml) was added
  7. stirringThe resulting solution was stirred at r.t. for 6 hours
  8. filtrationfiltered
  9. custompurified by prep

Sources & evidence

ORD record
ord-018e4ef4678a44a9b372d1033fbb2ddf
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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