Sodium Hydroxide → HCID 57514844, compound

HRID 1807456Notes

Reaction equation

HRID 1807456 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][C@@H:16]3[CH2:18][C@H:13]2[CH2:14][N:15]3[C:19](=[O:21])[CH3:20])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+:23]>C(Cl)Cl.CO.O>[C:19]([N:15]1[CH2:14][C@@H:13]2[CH2:18][C@H:16]1[CH2:17][N:12]2[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O-:4])=[CH:10][CH:9]=1)(=[O:21])[CH3:20].[Na+:23]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57514843HCID 57514843, compound

Product 1

HCID 57514844HCID 57514844, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[(1S,4S)-5-acetyl-2,5-diazabicyclo[2.2.1]hept-2-yl]methyl}phenyl acetate (2.33 g, 8.08 mmol, 1 equiv.) in CH2Cl2 (12.1 mL) and MeOH (8.1 mL) was added a solution of NaOH (0.323 g, 8.08 mmol, 1 equiv.) in water (4.1 mL). The solution was stirred at rt for 3 h. The reaction mixture was concentrated to afford product as an off-white solid (100%). 1H NMR (500 MHz, CD3OD): 7.01 (dd, J=8.8, 2.7, 2H), 6.61 (d, J=8.2, 2H), 4.63 (s, 0.5H), 4.41 (s, 0.5H), 3.63-3.53 (m, 4H), 3.35 (s, 3H), 3.28 (m, 0.5H), 3.19 (d, J=11.5, 0.5H), 2.91 (dd, J=10.3, 2.1, 0.5H), 2.82 (dd, J=10.2, 2.2, 0.5H), 2.67 (m, 1H), 1.94 (m, 1H), 1.76 (d, J=9.9, 0.5H), 1.66 (d, J=9.9, 0.5H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-650b616760b34f75bdf4f77ddde29e4f
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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