Diisopropylethylamine → ((4R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol

HRID 1446286

反応式

HRID 1446286 の反応式
[C:1]1([CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[O:56][N:55]=[CH:54][C:53]=2[C:57](O)=[O:58])=[CH:48][CH:47]=1>CN(C=O)C>[CH3:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]2[O:56][N:55]=[CH:54][C:53]=2[C:57]([N:10]2[CH2:11][C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]([CH2:12][OH:13])[CH2:9]2)=[O:58])=[CH:50][CH:51]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13316928(4-Phenylpyrrolidin-3-yl)methanolHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acid

生成物 1

HCID 68684409((4R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol収率 33.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (4-phenylpyrrolidin-3-yl)methanol (7 mg, 0.033 mmol), TBTU (13 mg, 0.039 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (11 μL, 0.066 mmol, 2 equ.) in DMF (0.3 mL) was added to 5-(4-methylphenyl)isoxazole-4-carboxylic acid (7 mg, 0.033 mmol) and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (4 mg). MS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1629.

後処理

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents the product
  4. customwas dried in vacuum

出典と根拠

ORDレコード
ord-de973918f5334992b12fc13abd8e2201
出典データセット
uspto-grants-2010_02
特許番号
US07666888B2

関連ノート

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