Iodoethane → 3-(2,3-Difluorophenyl)-1-ethylpyrrolidin-3-ol

HRID 1931825노트

반응식

HRID 1931825 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])([OH:13])[CH2:9]1)[C:2]1C=CC=CC=1.ICC.N1CCOCC1>CN(C)C=O>[F:21][C:15]1[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1([OH:13])[CH2:11][CH2:12][N:8]([CH2:1][CH3:2])[CH2:9]1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 8083MorpholineHCID 685158491-Benzyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol

생성물 1

HCID 251457763-(2,3-Difluorophenyl)-1-ethylpyrrolidin-3-ol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Preparation according to Example 34: (+)-1-benzyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol (0.40 g, 1.38 mmol), dimethyl formamide (3 mL), iodoethane (1.1 mL, 13.8 mmol) and morpholine (2 mL). Purification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 45:55). Yield: 0.11 g. [α]D=+19.8° (methanol). The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether/diisopropyl ether: M.p. 118-120° C.; MS m/z (relative intensity, 70 eV) 228 (M+, 14), 141, (16), 127 (14), 72 (26), 71 (bp).

후처리

  1. customPreparation
  2. customPurification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 45:55)
  3. customrecrystallized from methanol/diethyl ether/diisopropyl ether

출처 및 근거

ORD 기록
ord-628501d4d3254dca9a156d5318b05bbf
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188301B2

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