Tetrahydrofuran → tert-butyl 3(S)-[N-benzyl-N-(alpha(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate

HRID 635635

反応式

HRID 635635 の反応式
[CH2:1]([NH:8][C@@H:9]([CH3:16])[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.C([Li])CCC.[C:22]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH3:28].[Cl-].[NH4+].[O:37]1CCCC1>CCCCCC.C(OCC)C>[CH2:1]([N:8]([C@@H:24]([CH2:25][CH2:26][CH2:27][CH3:28])[C@H:23]([OH:37])[C:22]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C@@H:9]([CH3:16])[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

参加物

8

反応物 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 15636290(E)-tert-Butyl hept-2-enoateHCID 178418339Butyllithium

生成物 1

HCID 70091290tert-butyl 3(S)-[N-benzyl-N-(alpha(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A solution of 0.66 ml of (S)-(−)-N-benzyl-α-methylbenzylamine in 10 ml of tetrahydrofuran was cooled to 0° C. and 1.88 ml of a 1.6M solution of n-butyllithium in hexane were added dropwise via a syringe. The resulting dark pink solution was stirred at 0° C. for 45 minutes and then cooled to −78° C. A solution of 0.184 g of tert-butyl (E)-2-heptenoate in 2 ml of anhydrous diethyl ether was added and the mixture was stirred for 2 hours at −78° C. 0.37 g of solid (1S)-(+)-(10-camphorsulphonyl)oxaziridine was added and the mixture was stirred at −78° C. for 1 hour. The mixture was warmed to 0° C. and a saturated ammonium chloride solution was added. The tetrahydrofuran was evaporated and the aqueous phase was diluted with water and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, evaporated and purified by chromatography on silica gel using a 10% solution of diethyl ether in hexane for the elution to give 0.35 g of tert-butyl 3(S)-[N-benzyl-N-(α(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate as a colorless oil, MS: m/e 412.2 [M+H]+.

後処理

  1. temperaturecooled to −78° C
  2. stirringthe mixture was stirred for 2 hours at −78° C
  3. stirringthe mixture was stirred at −78° C. for 1 hour
  4. temperatureThe mixture was warmed to 0° C.
  5. customThe tetrahydrofuran was evaporated
  6. additionthe aqueous phase was diluted with water
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. customevaporated
  10. custompurified by chromatography on silica gel using a 10% solution of diethyl ether in hexane
  11. washfor the elution

出典と根拠

ORDレコード
ord-9aa01dd7d0e542f9b50491b1d3a049d4
出典データセット
uspto-grants-2001_02
特許番号
US06187905B1

関連ノート

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