Hydroxylamine → HCID 58305932, compound

HRID 2067851Notes

Reaction equation

HRID 2067851 reaction equation
CC1[N:3]([C@H:8]2[CH2:12][C@@:11]([C:23]3([OH:27])[CH2:26][CH2:25][CH2:24]3)([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH:10]=[CH:9]2)C(C)=CC=1.Cl.NO.NO.O>CO>[NH2:3][C@H:8]1[CH2:12][C@@:11]([C:23]2([OH:27])[CH2:24][CH2:25][CH2:26]2)([C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH:10]=[CH:9]1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 58305929Benzyl(1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(1-hydroxycyclobutyl)cyclopent-2-ene-1-carboxylate

Product 1

HCID 58305932HCID 58305932, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.52 g (15.1 mmol) of benzyl (1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(1-hydroxycyclobutyl)cyclopent-2-ene-1-carboxylate (Preparation SRT-0229), 8.20 g (120 mmol) of hydroxylamine hydrochloride, and 7.0 mL of 50% aqueous hydroxylamine (100 mmol) in 50 mL of methanol was heated at 68 C for 8 h, then cooled. Sufficient water was added to dissolve the crystals which deposited, and the solution was concentrated under reduced pressure to remove methanol. The resulting mixture was brought to pH ˜10 with aq. NaOH and then extracted with several portions of dichloromethane. The organic phase was dried over Na2SO4 and then concentrated under reduced pressure to afford 4.15 g (96%) of the title amine as a nearly colorless oil, of sufficient purity for the subsequent reaction. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42-1.53 (m, 1H) 1.85 (dd, 1H) 1.88-2.08 (m, 4H) 2.19-2.27 (m, 1H) 2.46 (dd, J=14.5, 8.3 Hz, 1H) 3.97-4.02 (m, 1H) 4.70 (s, 1H) 5.16 (s, 2H) 5.84 (dd, J=5.6, 1.6 Hz, 1H) 5.98 (dd, J=5.6, 2.1 Hz, 1H) 7.31-7.38 (m, 5H). LC-MS ES+ 288.2.

Workup

  1. temperaturewas heated at 68 C for 8 h
  2. temperaturecooled
  3. dissolutionto dissolve the crystals which
  4. concentrationthe solution was concentrated under reduced pressure
  5. customto remove methanol
  6. extractionextracted with several portions of dichloromethane
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84bdfdcdf742498db6689d85102f42cd
Source dataset
uspto-grants-2012_10
Patent number
US08293903B2

Reaction notes

Loading…