Potassium Hydroxide → HCID 70664308, compound

HRID 1808735Notes

Reaction equation

HRID 1808735 reaction equation
C([O:9][C@H:10]1[CH2:14][CH2:13][N:12]([C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:17])[CH3:16])[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[K+]>CO>[C:18]1([C:15]([N:12]2[CH2:13][CH2:14][C@H:10]([OH:9])[CH2:11]2)([CH3:17])[CH3:16])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 70664514HCID 70664514, compound

Product 1

HCID 70664308HCID 70664308, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (15 mL) solution of (3S)-1-(2-phenylpropan-2-yl)pyrrolidin-3-yl benzoate (2.50 g, 7.09 mmol) was added 4.0 M potassium hydroxide solution (3.19 mL, 12.8 mmol). The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL), washed with water (50 mL), dried (sodium sulfate), and concentrated in vacuo to afford the title compound as a white solid. This crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.42 (d, J=7.8 Hz, 2H), 7.32 (t, J=7.7 Hz, 2H), 7.21 (t, J=7.3 Hz, 1H), 4.52 (s, 1H), 4.40 (br s, 1H), 3.49-3.38 (m, 3H), 3.34 (d, J=11.0 Hz, 1H), 2.04-1.91 (m, 2H), 1.71 (s, 6H); LC-MS: m/z 249.2 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17e289728262491f8d4b6c4afdafe567
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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