Cyclopropanecarbonyl chloride → HCID 54073690, compound

HRID 2398032Notes

Reaction equation

HRID 2398032 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][N:7]3[NH:18][CH2:17][CH2:16][C@@:13]4([C:14]=2[CH:15]=1)[C@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12]4.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1>CCOCC.[OH-].[Na+]>[CH:19]1([C:22]([N:18]2[CH2:17][CH2:16][C@@:13]34[C:14]5[CH:15]=[C:2]([O:1][C:22]([CH:19]6[CH2:21][CH2:20]6)=[O:23])[CH:3]=[CH:4][C:5]=5[CH2:6][N:7]2[C@@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12]4)=[O:23])[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 54368747HCID 54368747, compound

Product 1

HCID 54073690HCID 54073690, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of 0.6 g of (+)-3-hydroxy-9-azamorphinan in 50 ml of Et2O and 20 ml of 20% NaOH aq. solution was added 1.0 g of cyclopropylcarbonyl chloride with stirring at room temperature. After stirring for 1 hr., the organic layer was washed (10% NaOH and then H2O), dried (K2CO3), and evaporated to give an oil, which was triturated with Et2O-pet. ether to form a solid. Recrystallization of this from Et2O afforded 0.5 g (53.5%) of (+)-N-cyclopropylcarbonyl-3-cyclopropylcarbonyloxy-9-azamorphinan as colorless plates; mp 144°-145.5.°.

Workup

  1. stirringAfter stirring for 1 hr
  2. wash, the organic layer was washed (10% NaOH
  3. dry with materialH2O), dried (K2CO3)
  4. customevaporated
  5. customto give an oil, which
  6. customwas triturated with Et2O-pet. ether
  7. customto form a solid
  8. customRecrystallization of this from Et2O

Sources & evidence

ORD record
ord-3ce31001c5e74d5583fbb659b0e02b96
Source dataset
uspto-grants-1977_05
Patent number
US04024082

Reaction notes

Loading…