(+-)-3-Quinuclidinol → 3-Quinuclidinyl 1-(2-bromophenyl)cyclobutanecarboxylate Hydrochloride

HRID 1955275노트

반응식

HRID 1955275 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:12]([Cl:14])=[O:13])[CH2:11][CH2:10][CH2:9]1.[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[CH:17]([OH:23])[CH2:16]2>>[ClH:14].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:12]([O:23][CH:17]2[CH:18]3[CH2:21][CH2:22][N:15]([CH2:20][CH2:19]3)[CH2:16]2)=[O:13])[CH2:11][CH2:10][CH2:9]1

참가 물질

3

반응물 2

HCID 15381(+-)-3-QuinuclidinolHCID 232950101-(2-Bromophenyl)cyclobutanecarbonyl chloride

생성물 1

HCID 232950283-Quinuclidinyl 1-(2-bromophenyl)cyclobutanecarboxylate Hydrochloride

실험 절차

The title compound was prepared in an analogous manner to that in Example 36. 1-(2-Bromophenyl)cyclobutanecarbonyl chloride, prepared from the compound prepared in Example 9, was reacted with 3-quinuclidinol at 75° C. overnight. The crude was chromatographed on silica gel using EtOAc-Et3N 90:10 as eluent. The yield was 0.2 g (6%); mp 194-200° C.; 1H NMR (CD3OD) δ 1.47-1.74 (m, 2H), 1.82-2.50 (m, 3H), 2.18-2.35 (m, 2H), 2.54-2.71 (m, 2H), 2.79-2.97 (m, 3H), 3.11-3.27 (m, 4H), 3.67-3.75 (m, 1H), 5.10 (m, 1H), 7.16-7.22 (m, 1H), 7.37-7.49 (m, 2H), 7.57 (dd, 1H). Anal. (C18H22BrNO2.HCl) C, H, N.

후처리

  1. customThe crude was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-d1bbec2a5d8043308628f4711390c9b3
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06124354

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