Hydrochloric Acid → 4-Phenyl-alpha,alpha,1-trimethyl-4-piperidinemethanol

HRID 1980094ノート

反応式

HRID 1980094 の反応式
[C:1]1([C:7]23[CH2:16][CH:11]([O:12][C:13]2([CH3:15])[CH3:14])[N:10]([CH3:17])[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].[BH4-].Cl.[OH-].[Na+]>CO.C(O)(=O)C>[C:1]1([C:7]2([C:13]([CH3:15])([CH3:14])[OH:12])[CH2:8][CH2:9][N:10]([CH3:17])[CH2:11][CH2:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28123BorohydrideHCID 5003444Sodium cyanoborohydrideHCID 540271932,6,6-Trimethyl-5-phenyl-7-oxa-2-azabicyclo[3.2.1]octane

生成物 1

HCID 133634034-Phenyl-alpha,alpha,1-trimethyl-4-piperidinemethanol収率 66.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

A solution of 1.47 g of the above product III in a mixture of 10 mL of methanol and 2 mL of acetic acid was cooled with ice and treated with 0.76 g of sodium cyanoborohydride. The mixture was stirred at room temperature for 2 h, and the excess borohydride was decomposed by addition, with ice cooling, of 8 mL of conc hydrochloric acid. After stirring at room temperature for 0.5 h the mixture was made basic with aqueous sodium hydroxide solution and extracted with methylene chloride. Removal of the solvent from the dried solution and crystallization of the residue from ethyl acetate gave 0.98 g of 4-phenyl-α,α,1-trimethyl-4-piperidinemethanol, m.p. 146°-147°. NMR (220 MHz in CDCl3): τ 2.7-2.8 (m, 5H); 7.0-8.2 (m, 9H); 8.0 (s, 3H) and 8.9 (s, 6H). Anal. Calcd. for C15H23NO: C, 77.21; N, 9.94; N, 6.00. Found: C, 77.12; H, 9.89; N, 6.00.

後処理

  1. temperaturewas cooled with ice
  2. stirringAfter stirring at room temperature for 0.5 h the mixture
  3. extractionextracted with methylene chloride
  4. customRemoval of the solvent
  5. customfrom the dried solution and crystallization of the residue from ethyl acetate

出典と根拠

ORDレコード
ord-fd47c0fcaa9c48a084c2ae5f515acf12
出典データセット
uspto-grants-1984_11
特許番号
US04485109

反応ノート

読み込み中…