Sodium borohydride → HCID 67362707, compound

HRID 1951349Notes

Reaction equation

HRID 1951349 reaction equation
[CH:1]([C:3]1[CH2:19][N:6]2[CH:7]=[CH:8][C:9]3[C:10]([CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=3)=[C:5]2[N:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH2:19][N:6]2[CH:7]=[CH:8][C:9]3[C:10]([CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=3)=[C:5]2[N:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86640848HCID 86640848, compound

Product 1

HCID 67362707HCID 67362707, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8 (40 mg, 0.16 mmol) in dry ethanol (5 mL), under argon, was added NaBH4 (9 mg, 0.24 mmol). The solution was stirred at room temperature for 30 min then the solvent was removed in vacuo. An aqueous saturated Na2CO3 solution (5 mL) was added and the solution was extracted with CH2Cl2 (3×20 mL). The organic layers were dried (MgSO4), filtered and evaporated to give compound 11 (23 mg, 57%); mp 227-229° C.; IR (KBr) 3289, 1685, 1266, 1191 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 1.38 (t, 3H, J=7 Hz), 4.38 (q, 2H, J=7 Hz), 4.60 (s, 2H), 5.17 (brs, 1H), 7.01 (d, 1H, J=7 Hz), 7.33 (s, 1H), 7.72 (s, 1H), 8.29 (d, 1H, J=7 Hz), 12.50 (brs, 1H); 13C NMR (100 MHz, DMSO-d6) δ 14.3, 58.0, 60.4, 101.1, 106.4, 110.3, 113.1, 124.4, 125.6, 133.1, 140.2, 144.7, 160.5; MS m/z 259 (M+, 60), 213 (52), 212 (100), 184 (22), 57 (25). Anal. Calcd for C13H13N3O3: C, 60.22; H, 5.05; N, 16.21. Found: C, 60.13; H, 5.18; N, 16.02.

Workup

  1. customthe solvent was removed in vacuo
  2. additionAn aqueous saturated Na2CO3 solution (5 mL) was added
  3. extractionthe solution was extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-21a87cc74f1e402ba76009594c29eafe
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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