3-(2-(Trifluoromethyl)phenyl)-2-propenoic acid → (+/-)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-ylcarbamate

HRID 390156ノート

反応式

HRID 390156 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:8][CH:7]2[NH:16][C:17](=[O:25])[O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22].[F:26][C:27]([F:40])([F:39])[C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[CH:30]=[CH:31][C:32](O)=[O:33].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][N:12]([C:32](=[O:33])/[CH:31]=[CH:30]/[C:29]3[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=3[C:27]([F:39])([F:40])[F:26])[CH2:11][CH2:10]1)[CH2:8][CH:7]2[NH:16][C:17](=[O:25])[O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 749393-(2-(Trifluoromethyl)phenyl)-2-propenoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67224539(+/-)-2-(Trimethylsilyl)ethyl 7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-3-ylcarbamate

生成物 1

HCID 67223014(+/-)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-ylcarbamate収率 47.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (±)-2-(trimethylsilyl)ethyl 7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-ylcarbamate (23 mg, 0.056 mmol), ortho-(trifluoromethyl)cinnamic acid (16 mg, 0.074 mmol) and i-Pr2NEt (0.027 mL, 0.15 mmol) in CH2Cl2 (3 mL) was added solid HATU (28 mg, 0.0.074 mmol). The mixture was stirred overnight at rt and evaporated to leave a residue which was purified by preparative HPLC to afford (±)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-ylcarbamate (16.5 mg, 47%). LC-MS Method 1 tR=2.37 min, m/z=623, 625.

後処理

  1. customevaporated
  2. customto leave a residue which
  3. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-380bef39935f46e6bc976562601e0820
出典データセット
uspto-grants-2013_02
特許番号
US08383629B2

反応ノート

読み込み中…