Methyl chloroformate → HCID 22141219, compound

HRID 1826386Notes

Reaction equation

HRID 1826386 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][OH:21])[CH:13]3[CH:9]2[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]3)[CH:5]=[CH:6][CH:7]=1.[CH2:22](N(CC)CC)C.Cl[C:30]([O:32][CH3:33])=[O:31].[C:34](=[O:37])([O-])[OH:35].[Na+]>O1CCCC1>[C:34](=[O:37])([O:35][CH3:22])[O:21][CH2:20][C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:30]([O:32][CH3:33])=[O:31])[CH:3]=2)[CH:13]2[CH:9]1[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]2

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22141155HCID 22141155, compound

Product 1

HCID 22141219HCID 22141219, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [6-(3-aminophenyl)-3-hexyl-3-azabicyclo[3.1.0]hex-6-yl]methanol (Preparation 94, 0.03 g, 0.09 mmol) in tetrahydrofuran (1 ml) was stirred at 0° C. under an atmosphere of nitrogen. The reaction mixture was treated with triethylamine (0.03 ml, 0.19 mmol) followed by dropwise addition of methyl chloroformate (0.01 ml, 0.17 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h before pouring onto aqueous saturated sodium hydrogen carbonate (50 ml). The product was extracted with ethyl acetate (3×25 ml) and the combined organic extracts were dried (Na2SO4) and then concentrated in vacuo to give a brown residue. The crude product was purified by preparative HPLC (condition 11) to give a clear glass (6 mg, 15% yield).

Workup

  1. extractionThe product was extracted with ethyl acetate (3×25 ml)
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a brown residue
  5. customThe crude product was purified by preparative HPLC (condition 11)

Sources & evidence

ORD record
ord-3771b377a2db44f8a4912952f3297b0e
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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