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

HRID 583385Notes

Reaction equation

HRID 583385 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[N:12]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[BH4-].[Na+]>CO.C1COCC1>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][OH:11])[C:5]=1[N:12]([S:21]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)(=[O:23])=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 867543143-Formyl-2-[(4-methoxy-benzenesulfonyl)-octyl-amino]-benzoic acid methyl ester

Product 1

HCID 700941703-Hydroxymethyl-2-[(4-methoxy-benzenesulfonyl)-octyl-amino]-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.547 g (1.187 mmol) of the product of Example 322 in 10 mL of methanol and 3 mL of THF was added 0.045 g (1.187 mmol) of sodium borohydride. The reaction was stired for 2 h at room temperature and then concentrated in vacuo. The residue was diluted with ether and washed with 5% HCl and water, dried over MgSO4, filtered and concentrated in vacuo to provide 0.549 g (100%) as a colorless oil. Electrospray Mass Spec: 464.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ether
  3. washwashed with 5% HCl and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide 0.549 g (100%) as a colorless oil

Sources & evidence

ORD record
ord-ab654ae12c004375a40792ff20c90b51
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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