tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-3-methylphenyl)piperidine-1-carboxylate

HRID 705775ノート

反応式

HRID 705775 の反応式
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=2)=[CH:14][C:13]=1[CH3:31])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]2)=[CH:14][C:13]=1[CH3:31]

参加物

4

反応物 1

HCID 68283391tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 68283578Tert-butyl 4-(4-amino-3-methylphenyl)piperidine-1-carboxylate収率 76.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A suspension of tert-butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I52) (798 mg, 2.49 mmol) and 10% Pd/C (250 mg) in MeOH (50 mL) was stirred under hydrogen (1 atm) for 16 hours at room temperature. The resulting mixture was filtered through celite, washing with MeOH, then the volatiles were removed by evaporation under reduced pressure to give the title compound (I53) (550 mg, 76%) as a purple/brown liquid; 1H NMR (400 MHz, CDCl3) δ 6.95 (d, J=6.7 Hz, 3H), 4.22 (s, 2H), 2.77 (s, 2H), 2.54 (s, 1H), 2.29 (s, 3H), 1.77 (d, J=12.7 Hz, 2H), 1.56 (dd, J=12.6, 3.7 Hz, 9H), 1.47 (s, 9H). LCMS Method C rt: 5.09 min; m/z 235.1 [M-tBu+2]+, 191.2 [M-Boc+2]+.

後処理

  1. filtrationThe resulting mixture was filtered through celite
  2. washwashing with MeOH
  3. customthe volatiles were removed by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-d6f46973230d44fe941fd77dc1dccb19
出典データセット
uspto-grants-2015_11
特許番号
US09174946B2

反応ノート

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