Potassium Carbonate → 4-[4-(2-Methyl-3-pyrrolidin-1-ylpropoxy)phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 272913노트

반응식

HRID 272913 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:17][CH:18]([CH3:25])[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:17][CH:18]([CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:25][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 225682631-(3-Chloro-2-methyl-propyl)-pyrrolidineHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

생성물 1

HCID 598375434-[4-(2-Methyl-3-pyrrolidin-1-ylpropoxy)phenyl]-tetrahydro-pyran-4-carbonitrile수율 96.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (790 mg, 3.87 mmol), 1-(3-chloro-2-methyl-propyl)-pyrrolidine (500 mg, 3.10 mmol), DMF (5 ml) and K2CO3 (2.14 g, 15.50 mmol) were reacted together according to general procedure E. The organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. to provide the title compound (979 mg, 96%) as a yellow solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.95 (d, 2H), 4.11-4.03 (m, 2H), 4.02 (dd, 1H), 3.89 (td, 2H), 3.77 (dd, 1H), 2.60-2.42 (m, 5H), 2.32 (dd, 1H), 2.22-1.99 (m, 5H), 1.82-1.72 (m, 4H), 1.07 (d, 3H).

후처리

  1. washThe organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C.

출처 및 근거

ORD 기록
ord-824472b7077a4822b65628bb2103b3ec
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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