Sodium borohydride → HCID 69780933, compound

HRID 1061539Notes

Reaction equation

HRID 1061539 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH:13]2[CH:8]([CH:9]=[C:10]([O:17][CH3:18])[C:11]([O:15][CH3:16])=[CH:12]2)[C:7]([C:19]2[CH:27]=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=2)=[N:6]1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH:13]2[CH:8]([CH:9]=[C:10]([O:17][CH3:18])[C:11]([O:15][CH3:16])=[CH:12]2)[CH:7]([C:19]2[CH:27]=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=2)[NH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69780950HCID 69780950, compound

Product 1

HCID 69780933HCID 69780933, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Intermediate 6 (1.5 g, 4.06 mmol) in MeOH (60 mL) was cooled to 0° C. and stirred under a nitrogen blanket. Sodium borohydride (154 mg) was added, and the resulting mixture was stirred for 2 hours. The reaction mixture then was concentrated in vacuo, during which time a white solid precipitated. The solid was triturated with MeOH (20 mL), collected by filtration, and dried to give 0.82 g (54%) of Intermediate 7: TLC Rf (90:10:1 CH2Cl2/EtOAc/MeOH)=0.33; 1H NMR (300 MHz, CDCl) δ: 6.84 (dd, J=7.8 Hz, J=1.6 Hz, 1H), 6.76-6.79 (m, 2H), 6.62 (s, 1H), 6.21 (s, 1H), 5.95 (dd, J=3.4 Hz, J=1.1 Hz, 2H), 5.02 (bs 1H), 3.82-3.86 (m, 1H), 3.86 (s, 3H), 3.78 (s, 3H) 3.64 (s, 3H), 3.01-3.14 (m, 2H), 2.41 (bs, NH); MS (API) m/z 372 (M+H).

Workup

  1. stirringthe resulting mixture was stirred for 2 hours
  2. concentrationThe reaction mixture then was concentrated in vacuo, during which time a white solid
  3. customprecipitated
  4. customThe solid was triturated with MeOH (20 mL)
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ac0dd0a28ac048a6998f04579584cfa5
Source dataset
uspto-grants-2005_11
Patent number
US06960587B2

Reaction notes

Loading…