Sodium borohydride → HCID 13330640, compound

HRID 2306565Notes

Reaction equation

HRID 2306565 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[C:12](=[O:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:4]=2[NH:3]1.[BH4-].[Na+]>CCO>[OH:19][CH:12]1[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[NH:3][C:4]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13802540HCID 13802540, compound

Product 1

HCID 13330640HCID 13330640, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 2 (2.5 g, 0.01 mol) in EtOH (25 mL) was added NaBH4 (3.75 g, 0.1 mol) at room temperature in small portions over 30 min. The reaction mixture was stirred for an additional 2 h and then cooled to 0° C. where it was triturated with dilute HCl (10% soln.). The resulting solid precipitated was filtered and washed with water and MeOH to provide 3a (2.326 g, 92%). 1H NMR (DMSO-D6): δ 5.58 (d, J=8.1 Hz, 1H), 5.78 (d, J=8.7 Hz, 1H), 7.33-7.89 (m, 6H), 7.95 (d, J=7.8 Hz, 1W, 8.22 (d, J=7.8 Hz, 1H), 12.29 (s, 1H); 3C NMR (DMSO-D6): δ 77.44, 118.81, 120.15, 124.28, 125.04, 125.67, 126.34, 128.46, 128.64, 128.95, 133.27, 135.62, 136.12, 139.93, 148.55, 163.69.; MS (ES+): m/z 250.1 (M+1); Anal. Calcd for C16H11NO2: C, 77.10; H, 4.45; N, 5.62. Found: C, 77.01; H, 4.57, N, 5.59.

Workup

  1. customwas triturated with dilute HCl (10% soln.)
  2. customThe resulting solid precipitated
  3. filtrationwas filtered
  4. washwashed with water and MeOH

Sources & evidence

ORD record
ord-9c6f34e95e964bb6bb46afe842da5ccc
Source dataset
uspto-grants-2004_12
Patent number
US06828319B2

Reaction notes

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