Methyl chloroformate → HCID 121006132, compound

HRID 1752845Notes

Reaction equation

HRID 1752845 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]([OH:11])[CH2:2]1.Cl[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+]>[NH4+].[Cl-]>[OH:11][C@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]([C:13]([O:15][CH3:16])=[O:14])[CH2:2]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 25223044HCID 25223044, compound

Product 1

HCID 121006132HCID 121006132, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of tetrahydroquinolin-3-ol 10 (200 mg, 1.34 mmol) and methyl chloroformate (1 mL, 13 mmol) in CH2Cl2H2O (4:1), was added K2CO3 (1.8 g, 13 mmol) at 0° C. and the reaction mixture was further allowed to stir for 6 h at 25° C. Progress of reaction was monitored by TLC and after completion of reaction, a saturated solution of NH4Cl (20 mL) was added. The organic layer was separated; the aqueous layer was extracted with CH2Cl2 (2×50 mL). Combined organic layers were washed with brine (2×25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude products. Chromatographic purification of crude product with petroleum etherethyl acetate (6:4 v/v) as eluent gave 11 (291 mg) as oily liquid.

Workup

  1. customProgress of reaction
  2. customafter completion of reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  5. washCombined organic layers were washed with brine (2×25 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude products
  9. customChromatographic purification of crude product with petroleum etherethyl acetate (6:4 v/v) as eluent

Sources & evidence

ORD record
ord-3998a52795ef4fbc86eb7646c49db18a
Source dataset
uspto-grants-2015_10
Patent number
US09163038B2

Reaction notes

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