Sodium borohydride → 3-Hydroxymethyl-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-benzoic acid methyl ester

HRID 583389Notes

Reaction equation

HRID 583389 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[N:12]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[BH4-].[Na+]>CO.C1COCC1>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][OH:11])[C:5]=1[N:12]([S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 867543163-Formyl-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-benzoic acid methyl ester

Product 1

HCID 701992853-Hydroxymethyl-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-benzoic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.10 g (0.227 mmol) of the product of Example 335 in 5 mL of methanol and 2.0 mL of THF was added 8.6 mg of sodium borohydride. The reaction was stirred for 1 h at room temperature and then concentrated in vacuo. The residue was diluted with dichloromethane, washed with water, and the organics were then dried over Na2SO4, filtered and concentrated in vacuo. The resulting tan solid was washed with ether and dried in vacuo to give 0.086 g (86%) of the alcohol. Electrospray Mass Spec: 442.9 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialthe organics were then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe resulting tan solid was washed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1354f32cac7b48adbb4874e3b521e8db
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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