Ammonia → Tert-butyl 3-{2-[2-(2-aminoethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176302노트

반응식

HRID 1176302 반응식
[N:1]([CH2:4][CH2:5][C:6]1[CH:48]=[CH:47][CH:46]=[CH:45][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH:12]1[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:13]1)=[N+]=[N-].N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O.CO.C(OCC)(=O)C>[NH2:1][CH2:4][CH2:5][C:6]1[CH:48]=[CH:47][CH:46]=[CH:45][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH:12]1[CH:17]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[CH:22][CH:23]=2)[CH2:16][CH2:15][N:14]([C:38]([O:40][C:41]([CH3:43])([CH3:44])[CH3:42])=[O:39])[CH2:13]1

참가 물질

8

반응물 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 86609993Tert-butyl 3-{2-[2-(2-azidoethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

생성물 1

HCID 68502787Tert-butyl 3-{2-[2-(2-aminoethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2.85 g of tert-butyl 3-{2-[2-(2-azidoethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 12.5 ml of tetrahydrofuran and 2.5 ml of water is admixed at room temperature with a solution of 1.2 ml of 25% conc. ammonia in 11.2 ml of methanol. After 1.7 g of triphenylphosphine have been added, the reaction mixture is stirred at room temperature over 16 hours. The mixture is diluted with ethyl acetate and washed with semisaturated aqueous sodium hydrogencarbonate solution (2×), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.17.

후처리

  1. washwashed with semisaturated aqueous sodium hydrogencarbonate solution (2×)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-3c24b7f6599d464198c6d8f10bc03faa
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

반응 노트

불러오는 중…