Ethanol → HCID 13424021, compound

HRID 1731619Notes

Reaction equation

HRID 1731619 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][CH:4]=[C:3]1[C:9]([C:11]1[N:15]2[CH2:16][CH2:17][CH:18]([C:19]([O:21][CH:22](C)[C:23]3C=CC=CC=3)=[O:20])[C:14]2=[CH:13][C:12]=1[CH3:30])=[O:10].B(Br)(Br)Br.C(O)C>C(Cl)Cl>[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][CH:4]=[C:3]1[C:9]([C:11]1[N:15]2[CH2:16][CH2:17][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]2=[CH:13][C:12]=1[CH3:30])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 13555838HCID 13555838, compound

Product 1

HCID 13424021HCID 13424021, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (-)-α-methylbenzyl 5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate (3.0 g, 7.1 mmol) in CH2Cl2 (80 ml) at -78° C. under N2 atmosphere was slowly added a 1.0M solution of boron tribromide in CH2Cl2 (15.6 ml, 15.6 mmol). The solution was stirred at -78° C. for 5 minutes and absolute ethanol (30 ml) was added slowly and warmed to room temperature then stirred at room temperature for 2 hours. The solution was washed with water (3×25 ml.) and brine (1×25 ml.), dried over anhydrous sodium sulfate, filtered and rotovapped at 20° C. to an orange solid and chromatographed on a flash silica gel column (5×15 cm) eluted with 50% ether/hexane. The resulting crude product was crystallized from hot EtOH to afford 2.12 g (86% yield) of (-)-ethyl 5-(1-methyl- 5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate. [α]D25 =-127.4 (CHCl3, C=1.06); m.p. 113°-115° C.

Workup

  1. temperaturewarmed to room temperature
  2. stirringthen stirred at room temperature for 2 hours
  3. washThe solution was washed with water (3×25 ml.) and brine (1×25 ml.)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customrotovapped at 20° C. to an orange solid
  7. customchromatographed on a flash silica gel column (5×15 cm)
  8. washeluted with 50% ether/hexane
  9. customThe resulting crude product was crystallized from hot EtOH

Sources & evidence

ORD record
ord-6718ee27550148f2a8ef6f6303120ec2
Source dataset
uspto-grants-1986_11
Patent number
US04622407

Reaction notes

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