Water → 1-{2-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}ethanol

HRID 1713084Notes

Reaction equation

HRID 1713084 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:32])[CH2:12][N:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:23]5C=CC(C(=O)C)=C[CH:24]=5)[CH:19]=4)[CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[OH2:35]>CCO>[CH:1]1([N:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:32])[CH2:12][N:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([CH:23]([OH:35])[CH3:24])[CH:19]=4)[CH2:14]3)[CH2:9][CH2:10]2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 247513731-(4-{2-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}phenyl)ethanone

Product 1

HCID 247512291-{2-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(4-{2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}phenyl)ethanone (153 mg) in EtOH (10 mL) is added sodium borohydride (20 mg). The resulting mixture is stirred at rt for 2 hr. Water (10.0 ml) is added to quench the reaction, and then the EtOH is evaporated. The residue is extracted with DCM (10 ml×3). The combined organic phase is dried over sodium sulfate, and the solvent is removed under reduced pressure to give a residue that is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.08˜7.14 (2H, m), 6.92-6.98 (1H, m), 4.82 (1H, q), 3.58-3.64 (6H, m), 3.28 (2H, s), 2.60-2.84 (6H, m), 2.20-2.28 (4H, m), 1.60-2.20 (6H, m), 1.42 (3H, d); MS (+VE) m/z 358.2 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe EtOH is evaporated
  4. extractionThe residue is extracted with DCM (10 ml×3)
  5. dry with materialThe combined organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customto give a residue that
  8. customis purified by PTLC (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-c9edf578463949908a66acdfdf170844
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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