Methyl chloroformate → HCID 85572223, compound

HRID 1009317Notes

Reaction equation

HRID 1009317 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH3:7].C(N(C(C)C)CC)(C)C.Cl[C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])O.[Na+]>ClCCl>[CH3:23][O:22][C:20](=[O:21])[NH:1][CH2:2][CH2:3][CH:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 55281593HCID 55281593, compound

Product 1

HCID 85572223HCID 85572223, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(±)-1-Amino-5-methyl-hex-4-en-3-ol (28.5 g, 219 mmol) and diisopropyl ethylamine (45.9 mL, 263 mmol) were dissolved in dichloromethane (400 mL) and cooled on an ice bath. Methyl chloroformate (17 mL, 219 mmol) in dichloromethane (20 mL) was added slowly. The mixture was stirred for 2 h. at 0° C. A saturated aqueous solution of sodium hydrogencarbonate was added and the phases separated. The aqueous phase was extracted twice with dichloromethane. The organic phases were dried, filtered and evaporated to give (±)-(3-hydroxy-5-methyl-hex-4-enyl)carbamic acid methyl ester (38.9 g, 100%) as a yellow oil.

Workup

  1. temperaturecooled on an ice bath
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  4. customThe organic phases were dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c043fc6052ff43eb822e486aa930b019
Source dataset
uspto-grants-2011_07
Patent number
US07973082B2

Reaction notes

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