Acetic Acid → HCID 10223040, compound

HRID 966531Notes

Reaction equation

HRID 966531 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][NH:22][CH3:23])[CH:18]=2)[NH:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:22]([CH3:23])[CH:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)[CH:18]=2)[NH:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 99669522-Methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 10223040HCID 10223040, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 2-methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic acid benzyl ester (403 mg, 1.25 mmol) and tetrahydro-4H-pyran-4-one (0.115 ML, 1.25 mmol) in dichloroethane (10 mL) was added sodium triacetoxyboro hydride (371 mg, 1.75 mmol) followed by acetic acid (0.071 mL, 1.25 mmol). The mixture was stirred at room temperature under nitrogen atmosphere for 3 hours and then partitioned between ethyl acetate and water. The organic phase was washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (5% methanol in methylene chloride) to give 270 mg (53%) of the desired product as a white foam: mp 109-11 1° C.; MS(APCI+): m/z 407.2 (MH+); Anal. Calcd for C25H30N2O3.0.25H2O: C, 73.05; H, 7.48; N, 6.82. Found: C, 72.86; H, 7.59; N, 6.78.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a solid residue, which
  7. customwas purified by chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-7c7b5e92742a423f9c9a127aa599d2a7
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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