Acetic Acid → (3R,4R)-4-(4-Bromo-2-nitro-phenylamino)-1-methyl-piperidin-3-ol

HRID 1670632노트

반응식

HRID 1670632 반응식
C=O.Cl.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[OH:18])=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=1.[C:22](O)(=O)C.C([BH3-])#N.[Na+]>O>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]2[CH2:17][CH2:16][N:15]([CH3:22])[CH2:14][C@H:13]2[OH:18])=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67334527HCID 67334527, 화합물

생성물 1

HCID 67334708(3R,4R)-4-(4-Bromo-2-nitro-phenylamino)-1-methyl-piperidin-3-ol수율 97%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Add formaldehyde (20.5 mL, 37-41% aqueous solution) to a solution of (3R,4R)-4-(4-bromo-2-nitro-phenylamino)-piperidin-3-ol.hydrochloride salt (0.0.024 mol, 8.68 g) and acetic acid (10.2 mL) in water (42 mL) and stir the reaction mixture at room temperature for 30 min. Add sodium cyanoborohydride (0.073 mol, 4.6 g) and stir the reaction mixture for 3 h. Quench the reaction mixture with sodium bicarbonate solution and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (7.8 g, 97%). 1H NMR (400 MHz, CDCl3) δ 1.63-1.71 (m, 1H), 2.16-2.21 (m, 2H), 2.33 (s, 3H), 2.35-2.38 (m, 1H), 2.60 (br s, 1H), 2.80 (d, 1H), 3.54-3.56 (m, 1H), 3.75-3.79 (m, 1H), 6.92 (d, 1H), 7.48 (dd, 1H), 8.14 (d, 1H), 8.30 (d, 1H).

후처리

  1. customQuench the reaction mixture with sodium bicarbonate solution
  2. extractionextract with dichloromethane
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

출처 및 근거

ORD 기록
ord-6eb42c0856d049e1bdb7fea96cfa16ea
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994164B2

반응 노트

불러오는 중…