Trifluoroacetic anhydride → 3(3-Methoxyphenyl)-N,N,2-trimethyl pentane-1-amine, (2R,3R)-

HRID 1096694노트

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HRID 1096694 반응식
[CH3:1][N:2]([CH3:18])[CH2:3][C@H:4]([CH3:17])[C@:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)(O)[CH2:6][CH3:7].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[H][H]>CC1CCCO1.[Pd]>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C@H:5]([CH2:6][CH3:7])[C@@H:4]([CH3:17])[CH2:3][N:2]([CH3:18])[CH3:1])[CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 9942979(alphaR)-alpha-[(1S)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanolHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 112533283(3-Methoxyphenyl)-N,N,2-trimethyl pentane-1-amine, (2R,3R)-수율 97.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 73012-Methyltetrahydrofuran용매

반응 조건

온도
5 °C

실험 절차

A solution of compound (4) (50.3 g) dissolved in 2-methyltetrahydrofuran (120 ml) was stirred and cooled to 5° C. Then trifluoroacetic anhydride (30.6 ml) was added slowly over a period of 10 minutes while the temperature of the reaction mixture was kept below 20° C. After addition, the reaction mixture was allowed to stir for 1 hour at 20° C. b) Palladium 10% on activated carbon (50% wetted) (2.52 g) was added and the reaction mixture was stirred at 800 rpm and pressurized to 2 atmosphere (202.65 kPa) with hydrogen gas. The reaction mixture was heated to 40° C. and stirred for 4 hours at 40° C. The mixture was allowed to cool to 20° C. and filtered under nitrogen atmosphere. The filter was washed with 2-methyltetrahydrofuran (10 ml). Water (160 ml) was added to the filtrate and the mixture was stirred, then an aqueous NaOH solution (28.6 ml, 50% w/w) was added over a period of 10 minutes while the temperature was kept below 20° C. The organic and water layer were allowed to separate, the organic layer was isolated and washed with water (50 ml), and concentrated under reduced pressure to dryness, yielding (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethyl-pentanamine (5) as a colourless oil (46.10 g).

후처리

  1. customwas kept below 20° C
  2. additionAfter addition
  3. additionwas added
  4. stirringthe reaction mixture was stirred at 800 rpm
  5. temperatureThe reaction mixture was heated to 40° C.
  6. stirringstirred for 4 hours at 40° C
  7. temperatureto cool to 20° C.
  8. filtrationfiltered under nitrogen atmosphere
  9. washThe filter was washed with 2-methyltetrahydrofuran (10 ml)
  10. additionWater (160 ml) was added to the filtrate
  11. stirringthe mixture was stirred
  12. additionan aqueous NaOH solution (28.6 ml, 50% w/w) was added over a period of 10 minutes while the temperature
  13. customwas kept below 20° C
  14. customto separate
  15. customthe organic layer was isolated
  16. washwashed with water (50 ml)
  17. concentrationconcentrated under reduced pressure to dryness

출처 및 근거

ORD 기록
ord-e4c3bb0756fa426abdc234e46f5d4273
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138376B2

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