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Triphenylphosphine → ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 603484
ノート
印刷プレビュー

反応式

HRID 603484 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12])[C:5]([CH3:14])=[CH:4][N:3]=1.O[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C@H:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:20][CH2:19]2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[CH2:9][CH2:10][CH2:11][O:12][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C@H:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:20][CH2:19]3)[C:5]([CH3:14])=[CH:4][N:3]=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 11776Triphenylphosphine2 回HCID 730421,1'-(Azodicarbonyl)dipiperidine2 回HCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 593004673-[(2-Chloro-5-methyl-4-pyrimidinyl)(methyl)amino]-1-propanol

生成物 1

HCID 59300440ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate
収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]-1-propanol (Example 341, 785 mg, 3.64 mmol) and ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 401 mg, 1.82 mmol) in THF (17 mL) were added PPh3 (954 mg, 3.64 mmol) and ADDP (918 mg, 3.64 mmol). The reaction mixture was vigorously stirred at rt for 24 h after which additional PPh3 (954 mg, 3.64 mmol) and ADDP (918 mg, 3.64 mmol) were added. After an additional 24 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (3:1 hexanes/EtOAc) to give the product (586 mg, 77%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.26 (t, 3H), 1.71-1.76 (m, 1H), 2.06-2.11 (m, 2H), 2.26 (s, 3H), 2.34-2.42 (m, 2H), 2.67-2.88 (m, 3H), 3.15 (s, 3H), 3.49-3.50 (m, 1H), 3.70 (t, 2H), 3.94 (t, 2H), 4.13 (q, 2H), 6.64 (d, 1H), 6.70 (s, 1H), 7.02 (d, 1H), 7.75 (s, 1H).

後処理

  1. additionwere added
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (3:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-8e690e4b745f4aa5bb80855c073f5f61
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07906653B2

反応ノート

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