Triethylamine → (R)-7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride

HRID 1899763

반응식

HRID 1899763 반응식
C([N:3]([CH2:6][CH3:7])CC)C.[Cl:8]C(OCC)=O.[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C@@H](C(O)=O)C2)=[CH:18][CH:17]=1.[N-]=[N+]=[N-].[Na+]>CC(C)=O.O>[ClH:8].[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C@@H:6]([NH2:3])[CH2:7]2)=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 147228187-methoxy-1,2,3,4-tetrahydro-(2R)-2-naphthoic acid

생성물 1

HCID 44784815(R)-7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride

시약·촉매·용매 2

HCID 180Acetone용매3회HCID 962Water용매2회

반응 조건

온도
-5 °C

실험 절차

A solution of 2 ml (0.0140 mol) of triethylamine in 20 ml of acetone and then 1.6 ml (0.0161 mol) of ethyl chloroformate in 20 ml of acetone are added slowly at a temperature of -10° C. to -5° C. to a solution of 2.5 g (0.0120 mol) of 7-methoxy-1,2,3,4-tetrahydro-(2R)-2-naphthoic acid in 30 ml of acetone. The mixture is stirred at -5° C. for 2 hours and a solution of 1.3 g (0.0193 mol) of NaN3 in 10 ml of water is then added dropwise. After 1 hour at -5° C., the mixture is poured into 200 ml of water and extracted with toluene. The two phases are separated, the organic phase is dried over sodium sulfate and filtered and the solution is heated at 100° C. for 1.5 hours. The solvent is evaporated off under reduced pressure, the residue is taken up with 22 ml of water and 26 ml of 37% hydrochloric acid and the mixture is refluxed for 3.5 hours. After cooling, the pH of the solution is rendered basic by the addition of 3.5 N NaOH, extraction is carried out with ethyl ether, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The hydrochloride of the base obtained in this way is prepared with a saturated solution of hydrochloric acid in ethyl ether. This gives 1.6 g of the title compound, which is crystallized from isopropanol to give 1.2 g of product. M.p. 205° C.-207° C.; [α]D20 =+66.6° (c=0.5%, MeOH).

후처리

  1. waitAfter 1 hour at -5° C.
  2. extractionextracted with toluene
  3. customThe two phases are separated
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. temperaturethe solution is heated at 100° C. for 1.5 hours
  7. customThe solvent is evaporated off under reduced pressure
  8. temperaturethe mixture is refluxed for 3.5 hours
  9. temperatureAfter cooling
  10. additionthe pH of the solution is rendered basic by the addition of 3.5 N NaOH, extraction
  11. dry with materialthe organic phase is dried over sodium sulfate
  12. customthe solvent is evaporated off under reduced pressure

출처 및 근거

ORD 기록
ord-d164b29ab66348eeb0720bea24de38f6
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05573949

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