Sodium borohydride → HCID 19735302, compound

HRID 326707Notes

Reaction equation

HRID 326707 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][C:6]1[C:7]([NH:22][S:23]([C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[N:8][CH:9]=[N:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.[BH4-].[Na+]>CO>[OH:31][CH2:30][C:29]1[CH:28]=[CH:27][C:26]([S:23]([NH:22][C:7]2[C:6]([CH2:5][C:4]3[CH:34]=[CH:35][CH:36]=[CH:37][C:3]=3[O:2][CH3:1])=[C:11]([O:12][CH2:13][CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:10]=[CH:9][N:8]=2)(=[O:24])=[O:25])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53682521HCID 53682521, compound

Product 1

HCID 19735302HCID 19735302, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

53 mg of rac-p-[[5-(o-methoxybenzyl)-6-[2-[(tetrahydro-2H-pyran-2-yl]oxy]ethoxy]-4-pyrimidinyl]sulfamoyl]benzalde-hyde were dissolved in 3 ml of methyl alcohol and treated with 37 mg of sodium borohydride at room temperature. After stirring at room temperature for 1 hour, the methanol was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and NaCl solution (saturated), dried and distilled under reduced pressure. There were obtained 42 mg of rac-α-hydroxy-N-[5-(o-methoxybenzyl)-6-[2-[(tetra-hydro-2H-pyran-2-yl)oxy]ethoxy]-4-pyrimidinyl]-p-toluene-sulfonamide as a colorless oil. MS: 529 (M); 445 (tetrahydro-2H-pyran-2-yl); 434 (--OCH3 +SO2).

Workup

  1. customthe methanol was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and NaCl solution (saturated)
  4. customdried
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-821affe0864647749aa63b8ef07cc106
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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