Sodium borohydride → HCID 22503724, compound

HRID 1813908Notes

Reaction equation

HRID 1813908 reaction equation
[C:1]([N:9]1[CH2:26][CH2:25][C:13]2[N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[C:12]=2[CH2:11][CH2:10]1)[C:17](=[O:24])[CH2:16][CH2:15]3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[C:1]([N:9]1[CH2:26][CH2:25][CH:13]2[N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[CH:12]2[CH2:11][CH2:10]1)[CH:17]([OH:24])[CH2:16][CH2:15]3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22503715HCID 22503715, compound

Product 1

HCID 22503724HCID 22503724, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-benzoyl-5,6,9,10,11,12-hexahydro-4H,8H-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-4-one (1.46 g, 4.24 mmol) in ethanol (40 mL) was cooled to 0° C. under N2. Added sodium borohydride (0.32 g, 8.46 mmol) and allowed to warm slowly to room temperature. Concentrated under reduced pressure to approximately 10 mL, diluted with H2O, and extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with EtOAc/heptanes (2:1) to give 1.24 g (84%) of the title compound as a yellow foam. 1H NMR (CDCl3) δ 7.42, 7.33, 7.12-7.02, 5.10, 4.13, 4.02, 3.68, 3.21, 2.92, 2.38, 2.23, 1.80; IR (drift) 1627, 1614, 1475, 1466, 1457, 1448, 1429, 1372, 1360, 1329, 1292, 1268, 785, 747, 706 cm−1; MS (ESI) 369.1 (M++Na).

Workup

  1. concentrationConcentrated under reduced pressure to approximately 10 mL
  2. additiondiluted with H2O
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customdecanted
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography with EtOAc/heptanes (2:1)

Sources & evidence

ORD record
ord-f4b5bb4cd8ba49e3b71862ebffb47b34
Source dataset
uspto-grants-2005_04
Patent number
US06875762B2

Reaction notes

Loading…