HCID 23433661, compound → HCID 23433459, compound

HRID 1938387Notes

Reaction equation

HRID 1938387 reaction equation
[C:1]([O:5][NH:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])=[CH:14][C:15]([CH3:20])([CH3:19])[NH:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C.C(O)C>[C:1]([O:5][NH:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]([CH3:21])[CH2:14][C:15]([CH3:20])([CH3:19])[NH:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 23433661HCID 23433661, compound

Product 1

HCID 23433459HCID 23433459, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To an oven-dried 100 mL round-bottomed flask containing 7-tert-butyloxycarbamoyl-1,2-dihydro-2,2,4-trimethylquinoline (EXAMPLE 147) (200 mg, 0.69 mmol) in 50 mL 2:1 ethyl acetate/ethanol at rt was added 10% Pd on C (approx 1 mol %), and the mixture was stirred under an atmosphere of H2 for 4 h. The reaction mixture was then filtered, and concentrated under diminished pressure to give 201 mg (quant) of 7-tert-butyloxycarbamoyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline as a white oily solid. Data for (R/S)-7-tert-butyloxycarbamoyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline: 1H NMR (400 MHz, CDCl3) 7.02 (d, J=8.7, 1H, 5-H), 6.73 (br s, 1H, HNBoc), 6.39 (dd, J=8.3, 2.2, 1H, 6-H), 6.29 (br s, 1H, 8-H), 3.62 (br s, 1H, NH), 2.85 (ddq, J=12.5, 12.3, 6.4, 1H, 4-H), 1.70 and 1.39 [d of ABq, JAB =12.8, JA =5.5 Hz (3-Hequiv), JB =12.6 Hz (3-Hax)2H], 1.49 [s, 9H, (CH3)3CO)], 1.29 (d, J=6.7, 3H, 4-CH3), 1.21 (s, 3H, 2-CH3), 1-14 (s, 3H, 2-CH3).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated under diminished pressure

Sources & evidence

ORD record
ord-6fb06a5bf5a54714854b3f8ba6c287a3
Source dataset
uspto-grants-1997_12
Patent number
US05693646

Reaction notes

Loading…