Hydrochloric Acid → Benzyl 4-(4-methoxycarbonylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1712535ノート

反応式

HRID 1712535 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH:12]2[O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]3[O:37][CH2:36][C:35](=O)[N:34]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:33]=3[CH:44]=2)=[CH:7][CH:6]=1)=[O:4].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH:12]2[O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]3[O:37][CH2:36][CH2:35][N:34]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:33]=3[CH:44]=2)=[CH:7][CH:6]=1)=[O:4]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 169536Tetrabutylammonium borohydrideHCID 516892Sodium BicarbonateHCID 68500724benzyl 4-(4-methoxycarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

生成物 1

HCID 68501193Benzyl 4-(4-methoxycarbonylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

A solution of 3.92 g of benzyl 4-(4-methoxycarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate (Example 255d) in 50 ml of chloroform is admixed under argon with 4.27 g of tetrabutylammonium borohydride. The reaction solution is stirred at 60° C. over 19 hours and subsequently cooled to room temperature. 10 ml of 2N HCl and 50 ml of water are subsequently added dropwise. The suspension is stirred at room temperature over 10 minutes. The reaction mixture is poured onto 150 ml of aqueous sodium hydrogencarbonate solution and extracted with 800 ml of tert-butyl methyl ether. The organic phase is washed with 100 ml of water and 50 ml of brine, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.19 (2:1 EtOAc-heptane); Rt=5.34.

後処理

  1. temperaturesubsequently cooled to room temperature
  2. stirringThe suspension is stirred at room temperature over 10 minutes
  3. extractionextracted with 800 ml of tert-butyl methyl ether
  4. washThe organic phase is washed with 100 ml of water and 50 ml of brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-7e06ccfce2884be7a5ab9ee975d07524
出典データセット
uspto-grants-2010_09
特許番号
US07790715B2

反応ノート

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