Cyclopropanemethanol → HCID 118080486, compound

HRID 1485714Notes

Reaction equation

HRID 1485714 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.ClC(Cl)(O[C:10](=[O:16])OC(Cl)(Cl)Cl)Cl.C(N(CC)C(C)C)(C)C.[Br:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]([C:38](=[O:40])[CH3:39])[C@@H:33]([CH3:41])[CH2:32][NH:31]2>ClCCCl.O>[C:38]([N:34]1[C:35]2[C:30](=[CH:29][C:28]([Br:27])=[CH:37][CH:36]=2)[N:31]([C:10]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[O:16])[CH2:32][C@@H:33]1[CH3:41])(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 75644CyclopropanemethanolHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 118078861(S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

Product 1

HCID 118080486HCID 118080486, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 250-mL round-bottom flask was charged with cyclopropylmethanol (1.90 g, 26.3 mmol), triphosgene (1.50 g, 5.28 mmol), N,N-diisopropylethylamine (4.0 mL, 23 mmol) and 1,2-dichloroethane (100 mL). The resulting solution was stirred for 1 h at 50° C. 1-[(2S)-6-Bromo-2-methyl-1,2,3,4-tetrahydroquinoxalin-1-yl]ethan-1-one (710 mg, 2.64 mmol) and N,N-diisopropylethylamine (4.0 mL, 23 mmol) in 1,2-dichloroethane (20 mL) were added, and the resulting solution stirred overnight at 50° C. After cooling to room temperature, the reaction mixture was poured into water (30 mL). The aqueous layer was separated and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via column chromatography on silica gel (eluting with 1:12, ethyl acetate/petroleum ether) to afford cyclopropylmethyl (3S)-4-acetyl-7-bromo-3-methyl-1,2,3,4-tetrahydroquinoxaline-1-carboxylate in (850 mg, 88%) as a yellow solid. MS (ESI, pos. ion) m/z 367, 369 [M+1]+.

Workup

  1. stirringthe resulting solution stirred overnight at 50° C
  2. temperatureAfter cooling to room temperature
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography on silica gel (eluting with 1:12, ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-129a153713c247f892a98f33e532035c
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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