tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)piperidine-1-carboxylate

HRID 1406621Notes

Reaction equation

HRID 1406621 reaction equation
[O:1]=[C:2]1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)=[CH:7][CH:8]=2)[NH:3]1>C1COCC1.[Pd]>[O:1]=[C:2]1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 1

HCID 117796386tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 117796385tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)piperidine-1-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 22 (0.8 g, 2.45 mmol) in THF (20 mL) was added Pd—C (10% wet basis, 0.15 g), and the mixture was subjected to hydrogenation in a Parr apparatus at 60 psi for 12 h. After filtering over the pad of celite, the solution was concentrated to get a brown oil material, which was resolved over silica column, eluting with hexanes:ethyl acetate (4:6) and then changing to (6:4) yielded 0.59 g (76%) of 23 as a light yellow gum. IR (KBr) νmax. cm−1: 3211, 3165 (NH), 3072 (Ar—H), 1698 (C═O), 1610, 1512, 1419 (C═C). 1H-NMR (500 MHz, CDCl3) δ=1.48 (s, 9H, (CH3)3C); 1.54 (m, 2H, CH2); 1.75-1.82 (m, 2H, CH2); 2.56 (m, 1H, CH); 2.76 (br. s, 2H, CH2); 4.23 (br. s, 2H, CH2); 4.44 (s, 2H, CH2); 6.58 (m, 2H, H-7, H-8); 7.30 (m, 1H, d, J=8.3 Hz, H-5); 13C NMR (125.7 MHz, CDCl3) δ=28.38 (CH3)3C), 32.50 (CH2), 42.87 (CH2), 43.30 (CH), 47.88 (CH2), 66.36 (CH2), 79.53 (CH3)3C), 93.98 (aromatic-C), 113.24 (aromatic-C), 116.97 (aromatic-C), 117.68 (aromatic-C), 132.41 (aromatic-C), 134.49 (aromatic-C), 149.82 (aromatic-C), 152.48 (C═O), 154.69 (C═O). Calculated (%) for C18H25N3O3(331.19); C, 65.23; H, 7.60; N, 12.68. found (%); C, 65.12; H, 7.69; N, 12.55.

Workup

  1. filtrationAfter filtering over the pad of celite
  2. concentrationthe solution was concentrated
  3. customto get a brown oil material, which
  4. washeluting with hexanes:ethyl acetate (4:6)

Sources & evidence

ORD record
ord-e2f360b3d659420d9c341484ac70d8a2
Source dataset
uspto-grants-2014_12
Patent number
US08916704B1

Reaction notes

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