Methanol → Benzyl 4-[((3R)-1-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine-1-carboxylate

HRID 603162ノート

反応式

HRID 603162 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13]O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.I([O-])(=O)(=O)=O.[NH:42]1[CH2:47][CH2:46][CH2:45][C@@H:44]([CH2:48][N:49]2[CH2:54][CH2:53][N:52]([C:55]([O:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[O:56])[CH2:51][CH2:50]2)[CH2:43]1.CO>C(Cl)Cl.S([O-])([O-])(=O)=O.[Mg+2]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][N:42]2[CH2:47][CH2:46][CH2:45][C@@H:44]([CH2:48][N:49]3[CH2:50][CH2:51][N:52]([C:55]([O:57][CH2:58][C:59]4[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=4)=[O:56])[CH2:53][CH2:54]3)[CH2:43]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

参加物

7

反応物 4

HCID 887MethanolHCID 59846067Benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylateHCID 67220797Benzenepropanol, 4-(methylsulfonyl)-HCID 131723735Dess-Martin Periodate

生成物 1

HCID 57656816Benzyl 4-[((3R)-1-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine-1-carboxylate収率 85.2%

試薬・触媒・溶媒 2

HCID 24083Sulfuric acid magnesium salt (1:1)触媒HCID 6344Dichloromethane溶媒2 回

実験手順

3-[4-(Methylsulfonyl)phenyl]propan-1-ol (4.02 g, 18.8 mmol) and Dess-Martin periodate (8.49 g, 20.0 mmol) were stirred in DCM (50 ml) at room temperature overnight. The reaction was washed with NaOH solution (1N, 3×25 ml). Sodium triacetoxyborohydide (5.28 g, 25 mmol) was added to the mixture followed by benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylate (3.97 g, 12.5 mmol) and magnesium sulphate (20.0 mg). The reaction was stirred at room temperature overnight then washed with water (20 ml) and dried using a phase separation cartridge. Silica was added and the solvent removed under reduced pressure to provide a cake which was added to the top of a silica column. Flash column chromatography (silica, 1%-10% MeOH:DCM) gave the title compound as a yellow oil (5.47 g, 85%).

後処理

  1. washThe reaction was washed with NaOH solution (1N, 3×25 ml)
  2. additionSodium triacetoxyborohydide (5.28 g, 25 mmol) was added to the mixture
  3. washthen washed with water (20 ml)
  4. customdried
  5. customa phase separation cartridge
  6. additionSilica was added
  7. customthe solvent removed under reduced pressure
  8. customto provide a cake which
  9. additionwas added to the top of a silica column

出典と根拠

ORDレコード
ord-d0fa8fb2b68e4dcdb4d074a26f94d5d0
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

反応ノート

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