HCID 57608496, compound → HCID 90444194, compound

HRID 2277067Notes

Reaction equation

HRID 2277067 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH:13]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([I:30])[CH:25]=1)[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[I:30][C:26]1[CH:25]=[C:24]([C:13](=[O:12])[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 57608496HCID 57608496, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 90444194HCID 90444194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Molecular sieves (20.0 g) and PCC (28.0 g, 127 mmol) were added portionwise to a stirred solution of tert-butyl (3-hydroxy-3-(3-iodophenyl)propyl)carbamate (16) (40.0 g, 106 mmol) in anhydrous CH2Cl2 (500 mL) under argon atmosphere at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 20 min. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water (300 mL), extracted with EtOAc (2×300 mL), washed with brine (300 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (100-200 silica mesh, 15-20% EtOAc-hexane) gave tert-butyl (3-(3-iodophenyl)-3-oxopropyl)carbamate (17) as a pale yellow oil. Yield (21.0 g, 54%); 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.95-7.91 (m, 2H), 7.21 (t, J=8.0 Hz, 1H), 3.57-3.51 (m, 2H), 3.18-3.12 (m, 2H), 1.83-1.76 (m, 1H), 1.45 (s, 9H); MS: m/z 378.12 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water (300 mL)
  3. extractionextracted with EtOAc (2×300 mL)
  4. washwashed with brine (300 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (100-200 silica mesh, 15-20% EtOAc-hexane)

Sources & evidence

ORD record
ord-75b10e306acf4cb48331c1f9b7b41816
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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