Ethyl Acetate → HCID 21868714, compound

HRID 392096Notes

Reaction equation

HRID 392096 reaction equation
C([BH3-])#N.[Na+].[I:5][C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[C:11]3[CH2:18][NH:17][CH2:16][CH2:15][N:12]3[C:13]=2[CH:14]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(O)(=O)C>[I:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH:11]3[CH2:18][NH:17][CH2:16][CH2:15][N:12]3[C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 21868721HCID 21868721, compound

Product 1

HCID 21868714HCID 21868714, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (95%, 1.6 g, 24 mmol) was added over 3 mm to a stirred solution of 7-iodo-1,2,3,4-tetrahydropyrazino-[1,2-a]indole (2.2 g, 7.4 mmol) in acetic acid (50 mL) at 10° C. under Ar. After complete addition the reaction was allowed to warm to room temperature and stirred for 18 h. The mixture was cautiously poured into a mixture of saturated aqueous sodium hydrogen carbonate solution (150 mL) and ethyl acetate (100 mL). The mixture was partitioned and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (1×100 mL), dried (magnesium sulfate), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide, (90:9:1)] to give the product as a yellow oil (1.74 g, 79%) which was used immediately.

Workup

  1. additionAfter complete addition the reaction
  2. customThe mixture was partitioned
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic extracts were washed with brine (1×100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent removed under vacuum
  8. customto leave a crude oil
  9. customThe oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide, (90:9:1)]

Sources & evidence

ORD record
ord-74f24ec97c45412c97ab4879a96ab806
Source dataset
uspto-grants-2004_10
Patent number
US06800627B1

Reaction notes

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