Triethylamine → beta-Amino-6-hydroxy-1,2,3,4-tetrahydro-beta-methyl-2-naphthaleneethanol

HRID 1802060ノート

反応式

HRID 1802060 の反応式
[NH2:1][C:2]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH3:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:2]1([CH3:5])[CH2:3][O:4][C:26](=[O:28])[NH:1]1)[CH2:15][CH2:14]2

参加物

5

反応物 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 461946762-Amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol

生成物 1

HCID 46194675beta-Amino-6-hydroxy-1,2,3,4-tetrahydro-beta-methyl-2-naphthaleneethanol収率 54.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To 25 grams of 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol in 575 mL of dichloromethane was added 45 g of triethylamine. The mixture was cooled to 0° C., and kept below 5° C. while 21 g of triphosgene in dichloromethane was added dropwise. The mixture was stirred at 20-25° C. for 1.5 hrs. The reaction was followed by HPLC until the starting material disappeared. The mixture was concentrated under reduced pressure, 375 mL ethyl acetate was added to the residue. It was washed with water (50 mL×2), dried, decolorized with carbon, and concentrated and dried to afford 10 g of 4-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methyloxazolidin-2-one, M=261, purity 97%.

後処理

  1. additionwas added dropwise
  2. concentrationThe mixture was concentrated under reduced pressure, 375 mL ethyl acetate
  3. additionwas added to the residue
  4. washIt was washed with water (50 mL×2)
  5. customdried
  6. concentrationconcentrated
  7. customdried

出典と根拠

ORDレコード
ord-76f634132a144a5aade74431e84739b3
出典データセット
uspto-grants-2013_01
特許番号
US08349849B2

反応ノート

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