HCID 59316905, compound → HCID 59316961, compound

HRID 74432Notes

Reaction equation

HRID 74432 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]([OH: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>[OH: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 59316905HCID 59316905, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 59316961HCID 59316961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred suspension of PCC (42.3 g, 196 mmol) and Celite (43 g) in DCM (300 mL) was cooled to 0° C. To this was added carbamate 129 (35.0 g, 131 mmol), slowly over a period of 15 min. The reaction mixture was allowed to stir at room temperature for 2 h during which the transformation was found to be complete. The reaction mass was then filtered through a pad of Celite and the filter bed was washed with DCM. Concentration of the filtrate gave a black tarry mass which was purified by flash chromatography (30-50% Ethyl acetate-Hexanes gradient) to give tert-butyl 3-(3-hydroxyphenyl)-3-oxopropylcarbamate (145) as pale yellow solid. Yield (20.3 g, 58%): 1H NMR (400 MHz, CDCl3) δ 9.78 (s, 1H), 7.27-7.40 (m, 2H), 7.01 (dd, J=8.0, 1.6 Hz, 1H), 6.80-6.83 (m, 1H), 3.22-3.27 (m, 2H), 3.08 (t, J=6.8 Hz, 2H), 1.36 (s, 9H).

Workup

  1. filtrationThe reaction mass was then filtered through a pad of Celite
  2. washthe filter bed was washed with DCM
  3. customConcentration of the filtrate gave a black tarry mass which
  4. customwas purified by flash chromatography (30-50% Ethyl acetate-Hexanes gradient)

Sources & evidence

ORD record
ord-ad27dced6e8a4a35aa2d558fc1fd49ea
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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