Sodium Hydroxide → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propoxyamine

HRID 1977942Notes

Reaction equation

HRID 1977942 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[O:16][CH2:17][CH2:18][CH2:19][O:20][N:21]1C(=O)C2=CC=CC=C2C1=O)(=[O:11])=[O:10])#[N:2].[BH4-].[Na+].[OH-].[Na+]>C(O)C.O1CCCC1.O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[O:16][CH2:17][CH2:18][CH2:19][O:20][NH2:21])(=[O:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22722458n-[3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide

Product 1

HCID 227225313-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propoxyamineYield 85.1%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of N-[3-[3-(2-cyanophenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide (600 mg, 1.2 mmol), as prepared in the preceding step, in 40 mL of ethanol/tetrahydrofuran/water (2:1:1) was added sodium borohydride (230 mg, 6.0 mmol). The reaction mixture was stirred at ambient temperature overnight. The mixture was acidified (pH 1-2) and heated to 50° C. for 2 hours. After cooling to room temperature, the solution was adjusted to pH 8-9 with 2N NaOH. The mixture was extracted into ethyl acetate (3×50 mL), and the organic phase was washed with brine (50 mL) and dried over Na2SO4. After removing the solvent, the residue was purified by flash column chromatography (dichloromethane to 2% methanol in dichloromethane) to give the title compound as a colorless oil (370 mg, 85%). 1H-NMR (300 MHz, CDCl3) δ8.06 (m, 1H), 7.93 (m, 1H), 7.76 (m, 2H), 6.61 (s, 1H), 6.53 (s, 2H), 5.36 (br s, 2H), 3.94 (t, J=6.3 Hz, 2H), 3.78 (t, J=6.2 Hz, 2H), 2.23 (s, 3H), 1.99 (m, 2H).

Workup

  1. temperatureheated to 50° C. for 2 hours
  2. temperatureAfter cooling to room temperature
  3. extractionThe mixture was extracted into ethyl acetate (3×50 mL)
  4. washthe organic phase was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent
  7. customthe residue was purified by flash column chromatography (dichloromethane to 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c182a68093504aaaab71e722434cd3a7
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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