1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-Benzyl-4-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidine

HRID 380532노트

반응식

HRID 380532 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([OH:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([C@H:30]([CH3:34])[C:31](O)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([O:23][C:31](=[O:32])[C@H:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:34])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27246222-Phenylpropionic acid, (+)-HCID 183647871-Benzyl-4-(3-phenyl-2-hydroxypropyl)piperidine

생성물 1

HCID 599707671-Benzyl-4-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidine

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1 g (3.23 mmol) of 1-benzyl-4-(3-phenyl-2-hydroxypropyl)piperidine (Example 228, Step 2) and 0.775 g (5.16 mmol) of (S)-2-phenylpropionic acid in 10 mL of CH2Cl2 at 0° C. was added 1.32 g (6.9 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and 0.1 g of 4-(dimethylamino)pyridine. The reaction was stirred for 5 h and let warm to rt. To the reaction mixture was added 80 mL of CH2Cl2 and the mixture was washed three times with 10% NaOH solution. The organic layer was washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1) to give isomer 1a of the the title compound. Mass Spectrum (ESI) m/e=442 (M+1). [α]D=−3.7 (c=2.44, CHCl3).

후처리

  1. washthe mixture was washed three times with 10% NaOH solution
  2. washThe organic layer was washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1)

출처 및 근거

ORD 기록
ord-c3d1f61766b34d54bddfaa9103bbab75
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303593B1

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