Water → (r)-Salmeterol

HRID 1593210노트

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HRID 1593210 반응식
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:41])[CH2:13][N:14]([C@@H](C3C=CC=CC=3)CO)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:11][C:5]=2[CH2:4][O:3]1.O>C(O)C.[OH-].[OH-].[Pd+2]>[OH:3][CH2:4][C:5]1[CH:11]=[C:10]([C@@H:12]([OH:41])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:9]=[CH:8][C:6]=1[OH:7]

참가 물질

5

반응물 2

HCID 962WaterHCID 10120860(1R)-1-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl][6-(4-phenylbutoxy)hexyl]amino}ethanol

생성물 1

HCID 6604001(r)-Salmeterol수율 86.9%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매2회HCID 702Ethanol용매

실험 절차

A solution of (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl][6-(4-phenylbutoxy)hexyl]amino}ethanol (110 mg), in ethanol (75 ml), was hydrogenated over Pearlman's catalyst [Pd(OH)2, 60% H2O, 55 mg) for 18 h. The catalyst was removed by filtration and the residue washed with methanol. The combined filtrate and washings were concentrated and then applied to a 10 g SCX ion exchange cartridge. The cartridge was eluted with methanol (4 column volumes) and then with 10% aqueous 880 NH3 in methanol (3 column volumes). The ammoniacal eluent was concentrated under reduced pressure to give the title compound (69 mg) as a colourless oil.

후처리

  1. customfor 18 h
  2. customThe catalyst was removed by filtration
  3. washthe residue washed with methanol
  4. concentrationThe combined filtrate and washings were concentrated
  5. washThe cartridge was eluted with methanol (4 column volumes)
  6. concentrationThe ammoniacal eluent was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9f42cb86dba24e0781a900c8f0dd2d32
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294725B1

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