Lithium borohydride → N-(4-cyano-2-hydroxymethyl-benzyl)-N-(3,5-dimethyl-pyridin-2-ylmethyl)-2-nitro-benzene-sulfonamide

HRID 1592666Notes

Reaction equation

HRID 1592666 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]([CH2:26][C:27]1[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][N:28]=1)[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15].[Li+].[BH4-]>C1COCC1.CO>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([CH2:12][N:13]([CH2:26][C:27]2[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][N:28]=2)[S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])=[C:4]([CH2:3][OH:2])[CH:9]=1)#[N:11]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 672721615-Cyano-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(2-nitro-benzenesulfonyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 67271378N-(4-cyano-2-hydroxymethyl-benzyl)-N-(3,5-dimethyl-pyridin-2-ylmethyl)-2-nitro-benzene-sulfonamideYield 104.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-cyano-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(2-nitro-benzenesulfonyl)-amino]-methyl}-benzoic acid methyl ester (0.83 g, 1.68 mmol) dissolved in THF (30 mL) and MeOH (10 mL), LiBH4 (0.37 g, 16.8 mmol) was slowly added. The mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo and redissolved in CH2Cl2 (50 mL). Water (50 mL) was added and the resulting mixture was extracted with CH2Cl2 (4×50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give crude N-(4-cyano-2-hydroxymethyl-benzyl)-N-(3,5-dimethyl-pyridin-2-ylmethyl)-2-nitro-benzene-sulfonamide (0.82 g, 78%) as a yellow foam. 1H NMR (CDCl3) δ 2.16 (s, 3H), 2.25 (s, 3H), 4.58 (s, 2H), 4.67 (s, 2H), 4.76 (br s, 1H), 4.88 (s, 2H), 7.10 (s, 1H), 7.36 (m, 2H), 7.50 (m, 1H), 7.65-7.72 (m, 3H), 7.80 (s, 1H), 7.89 (d, 1H, J=7.5 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in CH2Cl2 (50 mL)
  3. additionWater (50 mL) was added
  4. extractionthe resulting mixture was extracted with CH2Cl2 (4×50 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-876ce87c192548189703d3d678fb68fc
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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