Carbon tetrabromide → 4-[4-(2-Bromo-ethyl)-4-hydroxy-piperidin-1-yl]-2-trifluoromethyl-benzonitrile

HRID 2233609노트

반응식

HRID 2233609 반응식
[OH:1][C:2]1([CH2:20][CH2:21]O)[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49]>ClCCl>[Br:49][CH2:21][CH2:20][C:2]1([OH:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 675011244-[4-Hydroxy-4-(2-hydroxy-ethyl)-piperidin-1-yl]-2-trifluoromethyl-benzonitrile

생성물 1

HCID 675025684-[4-(2-Bromo-ethyl)-4-hydroxy-piperidin-1-yl]-2-trifluoromethyl-benzonitrile수율 59.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of compound 27a (687 mg, 2.09 mmol) in anhydrous dichloromethane (10 mL) at 0° C. under argon were added potassium carbonate (1.16 g, 8.39 mmol), triphenylphosphine (1.1 g, 4.19 mmol) and carbon tetrabromide (1.39 g, 4.19 mmol). The solution was allowed to return to room temperature and stirred for 1 hr. The resulting solution was diluted with dichloromethane (50 mL) and filtered on a cotton plug. Purification of the resulting crude product by flash chromatography using ethyl acetate/hexane (2:8) gave the desired compound 28a (470 mg, 57%). 1H NMR (400 MHz, MeOD) δ: 1.72 (m, 4H), 2.11 (m, 2H), 3.37 (m, 2H), 3.54 (m, 2H), 3.77 (m, 2H), 7.18 (dd, 1H, J1=6.26 Hz, J2=2.62 Hz), 7.27 (d, 1H, J=2.07 Hz), 7.69 (d, 1H, J=8.83 Hz).

후처리

  1. customto return to room temperature
  2. filtrationfiltered on a cotton plug
  3. customPurification of the resulting crude product by flash chromatography

출처 및 근거

ORD 기록
ord-43ead16bd5f3488b9844c3c51ebd7d16
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709516B2

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