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Potassium Carbonate → 2-[(9R)-9-(2-{4H,5H,6H-thieno[2,3-c]pyrrol-5-yl}ethyl)-6-oxaspiro[4.5]decan-9-yl]pyridine

HRID 626485
ノート
印刷プレビュー

反応式

HRID 626485 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@:7]1([CH2:17][CH2:18][NH2:19])[CH2:16][C:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.C(NCC[C@]1(C2C=CC(F)=CC=2)CC2(CCCC2)OCC1)C1C=CC=CC=1.Br[CH2:48][C:49]1[S:50][CH:51]=[CH:52][C:53]=1[CH2:54]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[S:50]1[C:49]2[CH2:48][N:19]([CH2:18][CH2:17][C@:7]3([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:16][C:11]4([CH2:15][CH2:14][CH2:13][CH2:12]4)[O:10][CH2:9][CH2:8]3)[CH2:54][C:53]=2[CH:52]=[CH:51]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 140017072,3-Bis(bromomethyl)thiopheneHCID 68314305benzyl({2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethyl})amineHCID 68314401Trv-0109662

生成物 1

HCID 683137832-[(9R)-9-(2-{4H,5H,6H-thieno[2,3-c]pyrrol-5-yl}ethyl)-6-oxaspiro[4.5]decan-9-yl]pyridine

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To a stirred solution of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine (0.030 g, 0.115 mmol; prepared by following a sequence described for Compound 81 in dried ACN (5.8 mL) was added 2,3-bis(bromomethyl)thiophene (31.1 mg, 0.115 mmol) followed by addition of K2CO3 (79.62 mg, 0.576 mmol). After 30 min, LCMS showed that the reaction was done and the major peak had the corresponding mass to the desired product. It was then subjected to HPLC purification. HPLC purification method: Luna acid medium column, 10-50% acetonitrile in H2O over 15 min, followed by flashing with 100% acetonitrile, 0.1% TFA modifier was employed. The fractions containing the desired product were pooled, basified with 2N NaOH and extracted with DCM (3×20 mL). The combined organics were concentrated and purified with flash chromatography (10 g silica gel column, eluted by 0-10% MeOH in DCM, based upon TLC measurement: DCM/MeOH (10/1) Rf=0.60) to afford 5 mg of 2-[(9R)-9-(2-{4H,5H,6H-thieno[2,3-c]pyrrol-5-yl}ethyl)-6-oxaspiro[4.5]decan-9-yl]pyridine as a colorless oil in 12% yield. LCMS m/z 369 (M+1) observed.

後処理

  1. customprepared

出典と根拠

ORDレコード
ord-8566a7ef860a4a9a9ac548c11575a051
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309234B2

反応ノート

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