Diisopropylethylamine → 1-Methylene-3-(SR)-((4-(N-(benzylaminocarbonyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane

HRID 993209노트

반응식

HRID 993209 반응식
[CH2:1]=[C:2]1[CH2:6][C@@H:5]([CH:7]=O)[C@H:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.Cl.[CH2:16]([NH:23][C:24]([N:26]([CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH2:27][CH2:28][CH3:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:1]=[C:2]1[CH2:3][CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]([CH2:7][N:33]2[CH2:32][CH2:31][CH:30]([N:26]([C:24]([NH:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:25])[CH2:27][CH2:28][CH3:29])[CH2:35][CH2:34]2)[CH2:6]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 186777054-(n-(Benzylaminocarbonyl)-(n-prop-1-yl)amino)piperidine hydrochlorideHCID 22890980(+-)-trans-4-Methylene-2-phenylcyclopentanecarboxaldehyde

생성물 1

HCID 701578021-Methylene-3-(SR)-((4-(N-(benzylaminocarbonyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane수율 85.9%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (+−)-trans-4-methylene-2-phenylcyclopentanecarboxaldehyde from Step C (880 mg, 4.7 mmol) in 1,2-dichloroethane (50 mL) was added 4-(N-(benzylaminocarbonyl)-(N-prop-1-yl)amino)piperidine hydrochloride (1.62 g, 5.2 mmol) and DIPEA (1.0 mL, 5.7 mmol). After 15 min, sodium triacetoxyborohydride (2.0 g, 9.5 mmol) was added and the reaction was stirred at rt for 4 h. The reaction was diluted with methylene chloride, quenched with aq. sodium carbonate and extracted 3 times with methylene chloride. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by FC eluting with 60% ethyl acetate in hexanes to give the title product (1.8 g) as the free amine. MS (NH3/ESI): m/z 448 (M +1).

후처리

  1. customquenched with aq. sodium carbonate
  2. extractionextracted 3 times with methylene chloride
  3. washeach washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FC
  7. washeluting with 60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-f673f208e8704ea3a95c1555bc63236b
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472410B1

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