Sodium borohydride → HCID 10737291, compound

HRID 431290Notes

Reaction equation

HRID 431290 reaction equation
[CH3:1][CH:2]([O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=1[CH3:26])[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].[BH4-].[Na+]>CCO>[CH3:1][CH:2]([O:16][C:17]1[C:18]([CH3:26])=[CH:19][C:20]([CH2:21][OH:22])=[CH:23][C:24]=1[CH3:25])[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10689805HCID 10689805, compound

Product 1

HCID 10737291HCID 10737291, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added EtOH (0.5 mL) at r.t. to a mixture of 7e (50 mg, 0.14 mmol) and sodium borohydride (5 mg, 0.14 mmol) and allowed to sit for 1 hour. The reaction was quenched with 1 m HCl (0.5 mL) and poured into 5% NaHCO3 (15 mL). Aqueous workup (Et2O, MgSO4) followed by concentration in vacuo yielded 8e (27 mg, 54%) as a yellow oil: 1H NMR (270 MHz, CDCl3) d 1.56 (d, J=6.2 Hz, 3H), 2.18 (s, 6H), 3.95 (s, 3H), 4.04 (s, 3H), 4.56 (s, 2H), 5.73 (q, J=6.2 Hz, IH), 7.00 (s, 2H), 7.55 (s, 1H), 7.59 (s, 1H); 13C NMR (68 MHz, CDCl3) d 17.6, 23.4, 56.4, 56.5, 65.1, 76.2, 107.5, 109.2, 128.1, 131.0, 135.4, 136.1, 139.0, 147.9, 153.8, 154.6.

Workup

  1. customThe reaction was quenched with 1 m HCl (0.5 mL)
  2. additionpoured into 5% NaHCO3 (15 mL)
  3. concentrationAqueous workup (Et2O, MgSO4) followed by concentration in vacuo

Sources & evidence

ORD record
ord-816360417965446186761009ac6fa338
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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