Triethylamine → HCID 58911275, compound

HRID 1295807Notes

Reaction equation

HRID 1295807 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].Cl.[NH2:9][C:10]1([OH:13])[CH2:12][CH2:11]1.CCN(CC)CC>C1COCC1.C(=O)=O>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([NH:9][C:10]1([OH:13])[CH2:12][CH2:11]1)=[O:6]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 702254-Bromobutyryl chloride2×HCID 187951Cyclopropanol, 1-amino-, hydrochloride

Product 1

HCID 58911275HCID 58911275, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, 4-bromo-butyryl-chloride (1.69 g, 9.13 mmol) is added onto a suspension 1-aminocyclopropanol hydrochloride (1.0 g, 9.13 mmol; synthesized following the method of Matthies, D.; Buechling, U. in Arch.Pharm.(Weinheim Ger.) 1983, 316, 598–608) and Et3N (2.21 g, 0.022 mol. in dry THF (20 ml at 0° C.). After 4 h, the reaction mixture is left overnight in dry ice and another portion of 4-bromo-butyryl-chloride (0.34 g) and Et3N (0.44 g) are added. After 2 h at room temperature, the reaction mixture is cooled down to 0° C., filtrated and concentrated in vacuo to give the crude 4-bromo-N-(1-hydroxy-cyclopropyl)-butyramide a16 which is used in the next step without any further purification.

Workup

  1. customsynthesized
  2. waitAfter 2 h at room temperature
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b556f4d92b4b4c97988a6e7bfee624e5
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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