Methyl chloroformate → HCID 22338728, compound

HRID 585018Notes

Reaction equation

HRID 585018 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C([O-])([O-])=O.[K+].[K+].[CH3:15][O:16][C:17](Cl)=[O:18]>O>[CH3:15][O:16][C:17]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:18]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 199606-Amino-1-hexanol

Product 1

HCID 22338728HCID 22338728, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 6-aminohexanol in 50 ml of water basified with 11 g of K2CO3, was added 4.03 g of methylchloroformate at room temperature. After one night the resulting aqueous solution was extracted with 3×50 ml of dichloromethane. The organic phases were combined, evaporated to dryness and the residue was filtered over silica gel. This furnished 1.36 g (yield 91%) of N-methoxycarbonyl-6-aminohexanol as a white solid. Then, to a solution of N-methoxycarbonyl-6-aminohexanol (200 mg) in dichloromethane (5 ml) was added 361 mg of triphenylphosphine and 832 mg of tetrabromomethane.

Workup

  1. extractionAfter one night the resulting aqueous solution was extracted with 3×50 ml of dichloromethane
  2. customevaporated to dryness
  3. filtrationthe residue was filtered over silica gel

Sources & evidence

ORD record
ord-dd0818f7bc904761b5665e695fd66d02
Source dataset
uspto-grants-2005_08
Patent number
US06929685B2

Reaction notes

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