Ammonium Chloride → HCID 86584095、化合物

HRID 850604

反応式

HRID 850604 の反応式
[CH2:1]([NH:8][C@H:9](C)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Li])CCC.[CH3:22][O:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=1.[NH4+].[Cl-]>C1COCC1.CCCCCC.CCOC(C)=O>[CH2:35]([O:34][C:32](=[O:33])[C@H:31]([CH3:17])[C@@H:30]([C:27]1[CH:28]=[N:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:36]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 1268086(+)-BenzylphenethylamineHCID 53930754HCID 53930754、化合物HCID 178418339Butyllithium

生成物 1

HCID 86584095HCID 86584095、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of N-benzyl-(R)-α-methylbenzylamine (97.5 g, 462 mmol) in THF (750 mL) at 0° C. was added n-butyllithium (2.5M in hexanes; 178.5 mL, 446 mmol). The dark violet solution was stirred at 0° C. for 20 minutes, cooled to -78° C. and the ester 7-3 (63.7 g, 308 mmol) in THF (250 mL) was added over 60 minutes. The resulting solution was stirred at -78° C. for 1 hr., then cannulated into saturated NH4Cl and extracted with EtOAc, washed with water then brine, dried and concentrated in vacuo to give an oil. Column chromatography (silica gel; hexane/EtOAc 9:1 then 4:1) gave 7-4 as an oil contaminated with N-benzyl-(R)-α-methylbenzylamine. This oil was taken up in 5% AcOH in water and extracted with diethyl ether (4×). The organic layers were dried over MgSO4 and the solvent removed to give the title compound 7-4. 1H NMR (300 MHz, CDCl3) δ 1.08 (3H, t), 1.27 (3H, d), 2.52 (1H, dd), 2.62 (1H, dd), 3.66 (1H, d), 3.70 (1H, d), 3.93 (3H, s), 3.95 (2H, m), 4.41 (1H, dd), 6.74 (1H, d), 7.15-7.45 (10H, m), 7.64 (1H, dd), 8.15 (1H, d).

後処理

  1. temperaturecooled to -78° C.
  2. stirringThe resulting solution was stirred at -78° C. for 1 hr
  3. extractionextracted with EtOAc
  4. washwashed with water
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customto give an oil

出典と根拠

ORDレコード
ord-55bbc0bdfc8c44d09d47eedb4c1452f1
出典データセット
uspto-grants-2000_01
特許番号
US06017926

関連ノート

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