Hydroxylamine → HCID 58305932, compound

HRID 1844315Notes

Reaction equation

HRID 1844315 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 than 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. concentrationthan concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3fcddb48c474c67b4f770cef5f6814f
Source dataset
uspto-grants-2015_02
Patent number
US08946413B2

Reaction notes

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