Sodium borohydride → HCID 70008667, compound

HRID 1266018Notes

Reaction equation

HRID 1266018 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[N:15]2[C:16]3[C:12]([CH:13]=[CH:14]2)=[C:11]([CH:17]=[O:18])[CH:10]=[CH:9][C:8]=3[CH2:7][NH:6][CH2:5]1>CCO>[OH:18][CH2:17][C:11]1[CH:10]=[CH:9][C:8]2[CH2:7][NH:6][CH2:5][C:4](=[O:3])[N:15]3[C:16]=2[C:12]=1[CH:13]=[CH:14]3

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86758916HCID 86758916, compound

Product 1

HCID 70008667HCID 70008667, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.018 g, 0.466 mmol) was added to a suspension of 1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-7-carbaldehyde (Example 45, 0.050 g, 0.233 mmol) in 15 mL EtOH. The reaction mixture was refluxed for 1.5 h, cooled to rt and the solvent was evaporated. The residue was partitioned between 1% aq NaOH and EtOAc. The organic extract was dried over anhydrous MgSO4, filtered and evaporated to give a pale-yellow solid (88%): 1H NMR (DMSO-d6) δ 3.52-3.55 (m, 2H), 4.31 (bs, 2H), 4.63 (d, 2H, J=5.0 Hz), 4.84 (t, 1H, J=5.0 Hz), 7.12 (t, 1H, J=7.5 Hz), 7.29 (s, 1H), 7.80-7.83 (m, 2H), 8.24-8.26 (m, 1H). HRMS calcd for C12H12N2O2 (M+) 216.0899, found 216.0908. Anal. (C12H12N2O2.0.2H2O) C, H, N.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 h
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between 1% aq NaOH and EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9b006a6f0f854edb913363af58661aed
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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