Sodium borohydride → HCID 19922465, compound

HRID 1463674Notes

Reaction equation

HRID 1463674 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[C:20]3[CH:19]=[C:18]([C:21](=[O:23])[CH3:22])[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[C:20]3[CH:19]=[C:18]([CH:21]([OH:23])[CH3:22])[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15296109HCID 15296109, compound

Product 1

HCID 19922465HCID 19922465, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 300 mg of 9,9-bis(4-pyridinylmethyl)-2-acetylfluorene was dissolved in 5 ml of ethanol cooled to 0° was added 100 mg of sodium borohydride. The reaction mixture was warmed to room temperature overnight, quenched with water and methanol and the solvents evaporated. The residue was partitioned between ethyl acetate and 1N NaOH, washed with water, brine, dried (MgSO4) and evaporated. Recrystallization from ethanol yielded product. NMR (CDCl3, 200 MHz) δ: 1.50(d,J=6.5 Hz, 3H), 3.39(s,4H), 4.92(q,J=6.4 Hz, 1H), 6.43(2d,4H), 7.08-7.58(m, arom.), 7.87(d,2H), 7.97(d,2H).

Workup

  1. temperaturecooled to 0°
  2. customquenched with water and methanol
  3. customthe solvents evaporated
  4. customThe residue was partitioned between ethyl acetate and 1N NaOH
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customRecrystallization from ethanol yielded product

Sources & evidence

ORD record
ord-97640bc2cd3b499fa415feea7fc26217
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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