六氢吡啶 → Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoate

HRID 36747

反应方程式

HRID 36747 反应方程式
[CH2:1]=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][SH:25].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][S:25][CH2:1][CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

参与物

6

反应物 4

HCID 8082六氢吡啶HCID 257982-甲胺乙硫醇盐酸盐HCID 66854苄基三甲基氢氧化铵HCID 10912012Benzyl 2-Benzylacrylate

产物 1

HCID 15296671Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoate收率 24%

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂2 次

实验过程

The oil prepared in Step 10 (1.5 g, 5.95 mmol) was dissolved under argon in methanol (22 mL). To this solution was added 2-dimethylaminoethanethiol hydrochloride (843 mg, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. The solvent was removed on a rotary evaporator and then the residue was purified by flash chromotography on silica gel, eluting with 20:1 CH2Cl2 :MeOH to give the pure title compound (0.5 g, 24% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C21H27NO2S+0.2H2O: C, 69.85; H, 7.65; N, 3.88. Found: C, 69.58; H, 7.60; N, 3.98.

后处理

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was purified by flash chromotography on silica gel
  3. washeluting with 20:1 CH2Cl2

来源与证据

ORD记录
ord-41f0d75e5d4744ac88a9dca12e15411d
来源数据集
uspto-grants-1995_05
专利号
US05416119

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