Ethyl Acetate → Phenylmethyl (2R)-2-((5-bromo-1H-indol-3-yl)carbonyl)-1-pyrrolidinecarboxylate

HRID 342024Notes

Reaction equation

HRID 342024 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11]([Mg]Cl)([CH3:14])([CH3:13])[CH3:12].C([O:20][CH2:21][CH3:22])(=O)C.[C:23](=[O:26])(O)[O-:24].[Na+]>C(OCC)C>[CH2:12]([O:24][C:23]([N:7]1[CH2:6][CH2:5][CH2:4][C@@H:22]1[C:21]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7][CH:6]=1)=[O:20])=[O:26])[C:11]1[CH:14]=[CH:3][CH:2]=[CH:10][CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 249055-BromoindoleHCID 516892Sodium BicarbonateHCID 178418310HCID 178418310, compound

Product 1

HCID 11224090Phenylmethyl (2R)-2-((5-bromo-1H-indol-3-yl)carbonyl)-1-pyrrolidinecarboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

N-Benzyloxycarbonyl-R-proline acid chloride from the above reaction was dissolved in anhydrous diethyl ether (30 mL) and added at 0° C. to a solution of 5-bromoindole (2.9 g, 15.0 mmol) and t-butylmagnesium chloride (2M solution in diethyl ether, 8.3 mL, 16.5 mmol) in anhydrous diethyl ether (30 mL). The resulting mixture was stirred at room temperature under argon for 45 minutes and then ethyl acetate (150 mL) and saturated sodium bicarbonate (30 mL) were added. The organic layer was dried and evaporated under reduced pressure to provide a yellow oil. The title compound was crystallized using hexane/ethyl acetate (9:1) to provide a white solid (3.07 g, 72%). mp 95°-96° C.

Workup

  1. customThe organic layer was dried
  2. customevaporated under reduced pressure
  3. customto provide a yellow oil
  4. customThe title compound was crystallized

Sources & evidence

ORD record
ord-df827a8b39584e36b5dbe0016db09aa8
Source dataset
uspto-grants-1999_01
Patent number
US05856510

Reaction notes

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