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

HRID 603162노트

반응식

HRID 603162 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24083Sulfuric acid magnesium salt (1:1)촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d0fa8fb2b68e4dcdb4d074a26f94d5d0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906645B2

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