Methanol → HCID 19961108, 화합물

HRID 1089011노트

반응식

HRID 1089011 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>ClC(Cl)C>[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 63651,1-Dichloroethane용매

실험 절차

A slurry of 10 g (25 mmol) of 1-aminomethyl-3,4-dihydro-5,6-dimethoxy-3-phenyl-naphthalene hydrochloride, from Step 2, in 150 mL of 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 recooled 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-3,4-dihydro-5,6-dihydroxy-3-phenyl naphthalene 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. temperatureto warm to ambient temperature
  3. concentrationconcentrated in vacuo
  4. additionTwice, 500 mL portions of methanol were added to the residue and it
  5. dissolutionThe resultant foam was dissolved in 40 mL of ethanol
  6. filtrationfiltered
  7. additionthe solution was treated with 40 mL of methylene chloride and 80 mL of heptane

출처 및 근거

ORD 기록
ord-1e2eab1a67184ef2adf772c850c6f921
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963568

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