Triethylamine → (1-Cyanocyclopropyl)methyl methanesulfonate

HRID 2090411Notes

Reaction equation

HRID 2090411 reaction equation
[OH:1][CH2:2][C:3]1([C:6]#[N:7])[CH2:5][CH2:4]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:8][S:9]([O:1][CH2:2][C:3]1([C:6]#[N:7])[CH2:5][CH2:4]1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 220282071-(Hydroxymethyl)cyclopropane-1-carbonitrile

Product 1

HCID 54220629(1-Cyanocyclopropyl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

At r.t. to a solution of 1-(hydroxymethyl)cyclopropanecarbonitrile (0.41 g, 4.2 mmol) in methylene chloride (10 mL) was added methanesulfonyl chloride (490 uL, 6.3 mmol), followed by triethylamine (1.5 mL, 10.0 mmol) and 4-dimethylaminopyridine (18 mg, 0.15 mmol). The mixture was stirred at r.t. for 3 h. It was diluted with methylene chloride, washed with water and brine, dried over Na2SO4. After filtration the filtrate was concentrated to yield the crude product which was used in the next step reaction without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration the filtrate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-66ee2b89c6fb4d1bbf8f17e053863ceb
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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