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Ammonia → 8-{[(2S)-2-(Hydroxymethyl)pyrrolidin-1-yl]sulfonyl}-3,3-dimethyl-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one

HRID 853864
ノート
印刷プレビュー

反応式

HRID 853864 の反応式
C([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[S:15]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][C:28]([CH3:32])([CH3:31])[C:29]#[N:30])[C:22](=O)[C:21]12OCCC[O:34]1)(=[O:17])=[O:16])C1C=CC=CC=1.N.C1COCC1>[Ni].CCO>[OH:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[S:15]([C:18]1[CH:26]=[CH:25][C:24]2[N:23]3[CH2:27][C:28]([CH3:32])([CH3:31])[CH2:29][N:30]=[C:22]3[C:21](=[O:34])[C:20]=2[CH:19]=1)(=[O:17])=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 589325233-[5'-({(2S)-2-[(benzyloxy)methyl]pyrrolidin-1-yl}sulfonyl)-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl]-2,2-dimethylpropanenitrile

生成物 1

HCID 115381048-{[(2S)-2-(Hydroxymethyl)pyrrolidin-1-yl]sulfonyl}-3,3-dimethyl-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one収率 84.3%

試薬・触媒・溶媒 2

HCID 935
Nickel
触媒
HCID 702Ethanol溶媒

反応条件

温度
132 °C

実験手順

A mixture of 3-[5′-({(2S)-2-[(benzyloxy)methyl]pyrrolidin-1-yl}sulfonyl)-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H)-yl]-2,2-dimethylpropanenitrile (3.00 g, 5.56 mmol), wet Raney Nickel (3.18 g) in 2M EtOH.NH3 (180 mL) and THF (30 mL) was hydrogenated at 54 lb/in2 H2 for 22 hr. The reaction was filtered through Sulka Floc and the filtrate was poured into a steel pressure vessel and heated to 132° C. for 18 hr. After cooling to room temperature the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (98.5/1/0.5) to give the title compound as a white solid (1.77 g, 60% ). NMR (400 MHz, DMSO-d6): consistent.

後処理

  1. customfor 22 hr
  2. filtrationThe reaction was filtered through Sulka Floc
  3. additionthe filtrate was poured into a steel pressure vessel
  4. temperatureAfter cooling to room temperature the reaction
  5. concentrationwas concentrated
  6. customThe crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (98.5/1/0.5)

出典と根拠

ORDレコード
ord-ba46ce6c6b79402d9a8286788b7fd429
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07256198B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート