Hydrochloric Acid → HCID 58566862, compound

HRID 2047945Notes

Reaction equation

HRID 2047945 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[C:17](=O)[NH:16][CH2:15][CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].B.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][NH:16][CH2:17]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 58566868HCID 58566868, compound

Product 1

HCID 58566862HCID 58566862, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7a-(3,4-Dichlorophenyl)octahydro-1H-isoindol-1-one (65 mg, 0.2287 mmol) was diluted in THF (2 mL) and borane (0.7 mL, 1 M in THF, 3 eq) and heated in the microwave for 15 minutes (max temp=100° C.). After cooling, the mixture was stirred with 6N HCl for thirty minutes and washed with MTBE. The aqueous layer was basicified with KOH and extracted with MTBE. The organic phase was evaporated and filtered (aminopropyl cartridge) to give 3a-(3,4-dichlorophenyl)octahydro-1H-isoindole (15.5 mg, 24%) as a clear oil. A further portion was later found in the organic wash and separated by silica gel filtration to give 19 mg (26%) additional product. LCMS Rt=7.60 min, m/z=270 (M+1). 1H NMR (CDCl3, δ): 7.43 (d, J=2.3 Hz, 1H), 7.37 (d, J=8.4 Hz, 1H), 7.19 (dd, J=2.3, 8.5 Hz, 1H), 3.1 (m, 2H), 2.9 (m, 1H), 2.6 (m, 2H), 2.0-1.2 (m, 8H). 13C NMR (CDCl3, δ, mult): 146.7(0), 132.3(0), 130.1(1), 129.7(0), 128.9(1), 126.2(1H), 59.9(2), 49.6(2), 47.9(0), 41.0(1), 32.8(2), 24.2(2), 22.0(2), 21.4(2).

Workup

  1. temperatureAfter cooling
  2. washwashed with MTBE
  3. extractionextracted with MTBE
  4. customThe organic phase was evaporated
  5. filtrationfiltered (aminopropyl cartridge)

Sources & evidence

ORD record
ord-34079043d3cf431f82673d722757865f
Source dataset
uspto-grants-2013_11
Patent number
US08592608B2

Reaction notes

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