Ethyl Acetate → HCID 22396842, compound

HRID 1356334Notes

Reaction equation

HRID 1356334 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl:29])[C:5]2[C:6]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17][C:7]=3[N:8]([CH2:11][C:12](OCC)=[O:13])[C:9]=2[CH:10]=1.[Li+].[BH4-].[OH-].[Na+].CCOC(C)=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:29])[C:5]2[C:6]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:18][CH2:17][C:7]=3[N:8]([CH2:11][CH2:12][OH:13])[C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 22396905HCID 22396905, compound

Product 1

HCID 22396842HCID 22396842, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 8,10-dichloro-6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (3.0 g, 6.8 mmol) in dry THF (30 mL) was cooled to 0° C. Then, LiBH4 (0.74 g, 34 mmol) was added and the reaction was allowed to warm slowly to rt. After 24 h, the reaction was diluted with H2O (75 mL) followed by addition of 10% aqueous NaOH (30 mL) and extraction with EtOAc (3×100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M, SIM) with heptane/EtOAc (1:1) followed by crystallization from EtOAc/heptane gave 1.6 g (58%) of a white solid: mp 166.5-167.0° C.; IR (diffuse reflectance) 3462, 1665, 1458, 1426, 1367, 1362, 1342, 1264, 1249, 1165, 1115, 1081, 931, 828, 820 cm−1; MS (EI) m/z 398 (M+), 398, 342, 341, 298, 270, 268, 258, 256, 57, 56; Anal. Calcd for C19H24Cl2N2O3: C, 57.15; H, 6.06; N, 7.01; found: C, 57.08; H, 6.08; N, 6.97.

Workup

  1. washThe combined organic extracts were washed with brine
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (Biotage, 40M, SIM) with heptane/EtOAc (1:1)
  6. customfollowed by crystallization from EtOAc/heptane

Sources & evidence

ORD record
ord-230a1fa782de4566844cca06d9612ede
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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