Water → (r)-Salmeterol

HRID 1593210ノート

反応式

HRID 1593210 の反応式
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]

参加物

5

反応物 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

生成物 1

HCID 6604001(r)-Salmeterol収率 86.9%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒2 回HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f42cb86dba24e0781a900c8f0dd2d32
出典データセット
uspto-grants-2007_11
特許番号
US07294725B1

反応ノート

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