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

HRID 709845노트

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HRID 709845 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-1a000f0120494f02bf6aed2cc66197cf
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181191B2

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