Methanol → HCID 59408995, compound

HRID 1894744Notes

Reaction equation

HRID 1894744 reaction equation
[CH2:1]1[C:9]2[C:4]3=[C:5]([CH:10]=[CH:11][N:3]3[CH2:2]1)[CH:6]=[CH:7][CH:8]=2.C(Cl)(=O)C(Cl)=[O:14].CO.[C:20]([O:23][CH2:24]C)(=[O:22])[CH3:21]>O1CCCC1>[CH3:24][O:23][C:20](=[O:22])[C:21]([C:1]1[C:9]2[C:4]3=[C:5]([CH2:10][CH2:11][N:3]3[CH:2]=1)[CH:6]=[CH:7][CH:8]=2)=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 21818461HCID 21818461, compound

Product 1

HCID 59408995HCID 59408995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,2-dihydro-pyrrolo[3,2,1-hi]indole (112 mg, 0.78 mmol) in anhydrous tetrahydrofuran (3 ml) at 0° C. was added oxalyl chloride (71 μl, 0.82 mmol). The mixture was stirred at 0° C. for 1 hour. Methanol (1 ml) was added and the mixture was allowed to warm to room temperature. After 30 minutes ethyl acetate (100 ml) was added and the mixture washed with water (100 ml) and brine (50 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness to give (4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-oxo-acetic acid methyl ester as a purple solid (153 mg). 400 MHz 1H NMR (CDCl3) δ: 8.32 (s, 1H), 7.86 (d, J=7.6 Hz, 1H), 7.23 (d, J=8.0 Hz, 1H), 7.08 (d, J=6.4 Hz, 1H), 4.60 (t, J=6.8 Hz, 2H), 3.95 (s, 3H), 3.84 (t, J=6.8 Hz, 2H); LCMS: 230 [M+H].

Workup

  1. temperatureto warm to room temperature
  2. washthe mixture washed with water (100 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-12d87a9cd17b499e941a0a96a57f1271
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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