Methanol → HCID 19961108, 화합물

HRID 233388노트

반응식

HRID 233388 반응식
Cl.[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:16]C)[C:10]([O:14]C)=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=1.B(Cl)(Cl)[Cl:25].CO>ClCCCl>[ClH:25].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([OH:16])[C:10]([OH:14])=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 19961156HCID 19961156, 화합물

생성물 1

HCID 19961108HCID 19961108, 화합물수율 56%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A slurry of 10 g (25 mmol) of 1-aminomethyl-5,6-dimethoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride, from Step 2, in 150 mL of 1,2-dichloroethane was cooled to 10° C. under a nitrogen atmosphere. Boron trichloride was passed through the reaction mixture until 27 g (230 mmol) had been added. The reaction mixture was allowed to warm to ambient temperature and stirred for 18 h. The reaction mixture was then cooled in ice and 100 mL of methanol was added dropwise. The reaction mixture was again allowed to warm to ambient temperature and concentrated in vacuo. Twice, 500 mL portions of methanol were added to the residue and it was reconcentrated. The resultant foam was dissolved in 40 mL of ethanol, filtered and the solution was treated with 40 mL of methylene chloride and 80 mL of heptane. Off-white crystals of 1-aminomethyl-5,6-dihydroxy-3-phenyl-3,4-dihydronaphthalene hydrochloride (5.1 g, 56% yield) were collected by filtration, m.p. 204°-205° C. The 1H NMR spectrum was identical to the spectrum for the product of Example 2A.

후처리

  1. additionhad been added
  2. temperatureThe reaction mixture was then cooled in ice
  3. temperatureto warm to ambient temperature
  4. concentrationconcentrated in vacuo
  5. additionTwice, 500 mL portions of methanol were added to the residue and it
  6. dissolutionThe resultant foam was dissolved in 40 mL of ethanol
  7. filtrationfiltered
  8. additionthe solution was treated with 40 mL of methylene chloride and 80 mL of heptane

출처 및 근거

ORD 기록
ord-6d94b33f9d1241cc9d8d19a0592b3b75
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591884

반응 노트

불러오는 중…