HCID 68941374, compound → HCID 68940433, compound

HRID 242727Notes

Reaction equation

HRID 242727 reaction equation
[OH:1][CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]2[C:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][CH2:24][C:23]=2[CH3:30])[CH:15]=1)[CH:3]([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl.O=[Mn]=O>[CH3:13][CH:3]([C:2](=[O:1])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]2[C:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][CH2:24][C:23]=2[CH3:30])[CH:15]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 1

HCID 68941374HCID 68941374, compound

Product 1

HCID 68940433HCID 68940433, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-tert-butyl 3-hydroxy-2-methyl-3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)propylcarbamate (0.2728 g, 0.64 mmol) in CH2Cl2 (10 mL) under argon was added MnO2 (2.4751 g, 28.5 mmol). The mixture was stirred at room temperature overnight. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (10 to 50% EtOAc-hexanes gradient) gave (E)-tert-butyl 2-methyl-3-oxo-3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)propylcarbamate as an oil. (Yield 0.1333 g, 49%): 1H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 6.75 (dd, J=16.4, 0.8 Hz, 1H), 6.38 (d, J=16.4 Hz, 1H), 4.96 (br s, 1H), 3.76-3.81 (m, 1H), 3.40 (t, J=6.0 Hz, 2H), 2.04 (t, J=6.0 Hz, 2H), 1.76 (s, 3H), 1.61-1.72 (m, 2H), 1.46-1.51 (m, 2H), 1.40 (s, 9H), 1.19 (d, J=7.2 Hz, 3H), 1.06 (s, 6H).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification by flash chromatography (10 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-e49a2a403ef94e12b9391b2cb4300c7d
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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