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Potassium Carbonate → ethyl (3S)-3-[4-[[4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate

HRID 390400
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HRID 390400 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[CH:46]=[CH:45][C:29]([CH2:30][N:31]2[CH2:36][CH2:35][C:34]3([C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37]3)[CH2:33][CH2:32]2)=[CH:28][CH:27]=1>C(#N)C>[N:31]1([CH2:30][C:29]2[CH:45]=[CH:46][C:26]([CH2:25][O:1][C:2]3[CH:3]=[CH:4][C:5]([C@@H:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)=[CH:27][CH:28]=2)[CH2:36][CH2:35][C:34]2([C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[CH:37]2)[CH2:33][CH2:32]1
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5

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HCID 11430Potassium CarbonateHCID 67087065Ethyl (3S)-3-(4-hydroxyphenyl)hex-4-ynoateHCID 670871851'-[4-(Bromomethyl)benzyl]spiro[indene-1,4'-piperidine]

생성물 1

HCID 58230558ethyl (3S)-3-[4-[[4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate수율 38.5%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
90 °C

실험 절차

To a solution of ethyl(3S)-3-(4-hydroxyphenyl)hex-4-ynate (0.350 g, 1.5 mmol) in acetonitrile (25 mL) is added potassium carbonate (0.621 g, 4.5 mmol) and 1′-[4-(bromomethyl)benzyl]spiro[indene-1,4′-piperidine] (0.77 g, 2.1 mmol). The reaction mixture is heated for 16 hours at 90° C. The mixture is concentrated, diluted with water, and extracted with EtOAc (2×200 mL). The combined extracts are washed with water (50 mL), brine (50 mL), dried over sodium sulfate, filtered, and concentrated to dryness to give the title compound (0.3 g, 38%). ESI/MS m/z 520 (M+H)+.

후처리

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc (2×200 mL)
  4. washThe combined extracts are washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-37c3d8d39fba4ade9333d18fbae73ae9
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08383642B2

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