Ammonia → 2-Methyl-N-(3-{1-[(3R)-3-Phenoxy-3-Phenylpropyl]-4-Piperidinyl}Phenyl)Propanamide

HRID 1832181ノート

反応式

HRID 1832181 の反応式
[OH:1][C@H:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1.[C:29]1(O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.N>C1COCC1.C(Cl)(Cl)Cl>[CH3:20][CH:19]([CH3:21])[C:18]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][C@@H:2]([O:1][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:6][CH2:7]2)[CH:12]=1)=[O:22]

参加物

8

反応物 5

HCID 222AmmoniaHCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 60078700N-(3-{1-[(3S)-3-Hydroxy-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

生成物 1

HCID 600786902-Methyl-N-(3-{1-[(3R)-3-Phenoxy-3-Phenylpropyl]-4-Piperidinyl}Phenyl)Propanamide収率 36%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of N-(3-{1-[(3S)-3-hydroxy-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide (9.53 mg, 0.0250 mmol), phenol (4.70 mg, 0.050 mmol), triphenylphosphine (9.80 mg, 0.0375 mmol) and diethyl azodicarboxylate (5.22 mg, 0.0300 mmol) in THF (1.0 mL) was stirred at room temperature for 3 days. Chromatography using silica preparative TLC plates [2.5% of NH3 (2.0 M in methanol) in CHCl3] gave the desired product (4.1 mg, 36.0% yield) as a thick oil: 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.40–7.15 (m, 10H), 6.97 (d, 1H, J=7.6 Hz), 6.88–6.82 (m, 2H), 5.26 (m, 1H), 3.18 (m, 2H), 2.75 (m, 2H), 2.53 (m, 2H), 2.40–2.10 (m, 4H), 2.10–1.80 (m, 4H), 1.25 (d, 6H, J=6.9 Hz); ESMS m/e: 457.4 (M+H)+.

出典と根拠

ORDレコード
ord-11711c099f8b4bd088252a2b8b7c8b71
出典データセット
uspto-grants-2006_06
特許番号
US07067534B1

反応ノート

読み込み中…