Bromomethylcyclopropane → HCID 86737781, compound

HRID 1680247Notes

Reaction equation

HRID 1680247 reaction equation
[OH:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][NH:18][C@@H:8]([C@@H:9]3[CH2:10][C@H:11]([CH3:20])[C:12](=[O:19])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:21][CH3:22].C([O-])(O)=O.[Na+].[CH:28]1([CH2:31]Br)[CH2:30][CH2:29]1>CN(C=O)C>[CH:28]1([CH2:31][N:18]2[CH2:17][CH2:16][C@@:14]34[C:15]5[C:2]([OH:1])=[C:3]([O:21][CH3:22])[CH:4]=[CH:5][C:6]=5[CH2:7][C@@H:8]2[C@@H:9]3[CH2:10][C@H:11]([CH3:20])[C:12](=[O:19])[CH2:13]4)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 86737779HCID 86737779, compound

Product 1

HCID 86737781HCID 86737781, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18a (5.00 g, 16.6 mmole), NaHCO3 (2.90 g, 34.6 mmole) and cyclopropylmethyl bromide (2.80 g, 20.8 mmole) in DMF (50 ml) was heated at 100° under argon for 2 hours. The mixture was cooled, filtered from insoluble material and the filtrate evaporated in high vacuum. The residue was dissolved in dilute NH4OH and extracted with three portions of toluene. The toluene was evaporated to give 4.89 g (83%) of crystalline 19a-CPM. Two recrystallizations from ethanol gave analytically pure 19a-CPM, mp 176.5°-178°. NMR: δ 6.56, s, 2H (aromatic); 6.17, S, 1H, (hydroxy proton); 4.23, d, 1H, (H-5α, J=12.5 Hz); 3.78 (CH3O--); 1.30, d, (H-5β); 0.87, d, 3H (7α-CH3, J=6.5 Hz),

Workup

  1. temperaturewas heated at 100° under argon for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered from insoluble material
  4. customthe filtrate evaporated in high vacuum
  5. dissolutionThe residue was dissolved in dilute NH4OH
  6. extractionextracted with three portions of toluene
  7. customThe toluene was evaporated
  8. customto give 4.89 g (83%) of crystalline 19a-CPM
  9. customTwo recrystallizations from ethanol
  10. customgave analytically pure 19a-CPM, mp 176.5°-178°

Sources & evidence

ORD record
ord-222d2f28c1084af9b1dfd7f4a666aef2
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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