Methanol → HCID 19961108、化合物

HRID 1089011ノート

反応式

HRID 1089011 の反応式
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

参加物

5

反応物 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 19961156HCID 19961156、化合物

生成物 1

HCID 19961108HCID 19961108、化合物収率 56%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e2eab1a67184ef2adf772c850c6f921
出典データセット
uspto-grants-1990_10
特許番号
US04963568

反応ノート

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