Sodium borohydride → HCID 22503724, compound

HRID 2186691Notes

Reaction equation

HRID 2186691 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]quinolin-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-223d992ebaa84827a53c8a2baf009c9c
Source dataset
uspto-grants-2002_06
Patent number
US06407092B1

Reaction notes

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