Sodium borohydride → Toluene-4-sulfonic acid 4-{[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-methyl}-phenyl ester

HRID 1827512Notes

Reaction equation

HRID 1827512 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1)=O.[N:20]1([CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1.[BH4-].[Na+]>CO.C(O)C>[N:20]1([CH2:25][CH2:26][O:27][C:28]2[CH:29]=[CH:30][C:31]([NH:34][CH2:1][C:3]3[CH:8]=[CH:7][C:6]([O:9][S:10]([C:13]4[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=4)(=[O:12])=[O:11])=[CH:5][CH:4]=3)=[CH:32][CH:33]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 51250864-(((4-Methylphenyl)sulfonyl)oxy)benzaldehydeHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 22137300Toluene-4-sulfonic acid 4-{[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-methyl}-phenyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of toluene-4-sulfonic acid 4-formyl-phenyl ester (3.28 g, 11.88 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (2.45 g, 11.88 mol) in 40 mL of methanol was stirred at room temperature overnight. The reaction mixture was concentrated to dryness. A portion of the crude residue (1.36 g, ˜2.92 mmol) was dissolved in 35 mL of ethanol and was treated with sodium borohydride (0.687 g, 18.16 mmol), which was added in portions over a period of about 3 hr. The reaction was stirred at room temperature overnight at which time it was concentrated to one-half of its original volume. To this mixture was added 25 mL of water and 25 mL of saturated sodium bicarbonate. The mixture was extracted three times with methylene chloride and the combined organic layers were dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography of the residue (2% methanol/methylene chloride to 10% methanol/methylene chloride) afforded 1.06 g (80%) of the title compound. MS 467.1 (M+1)+

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionwas added in portions over a period of about 3 hr
  3. concentrationwas concentrated to one-half of its original volume
  4. additionTo this mixture was added 25 mL of water and 25 mL of saturated sodium bicarbonate
  5. extractionThe mixture was extracted three times with methylene chloride
  6. dry with materialthe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a70a12dcde364a56938c1f9506648f50
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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