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Lithium borohydride → 1-(3-Hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 132918
ノート
印刷プレビュー

反応式

HRID 132918 の反応式
[Li+].[BH4-].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH2:29][CH2:30][C:31](OC)=[O:32])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH2:29][CH2:30][CH2:31][OH:32])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=3)[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4148881Lithium borohydride2 回HCID 684627001-(2-Methoxycarbonyl-ethyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

生成物 1

HCID 684611921-(3-Hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒
2 回

実験手順

A solution of LiBH4 (26 mg, 1.2 mmol) in THF (0.5 mL) was added to a 0° C. solution of 1-(2-methoxycarbonyl-ethyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (317 mg, 0.70 mmol) in THF (4.0 mL). The mixture was stirred for 5 min then additional LiBH4 (15 mg) was added and stirring continued for 17 h. The mixture was partitioned between EtOAc (80 mL) and saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined extracts were dried over Na2SO4 and concentrated. Column chromatography (silica, 0-8% MeOH/CH2Cl2) afforded 268 mg (95%) of the title compound. HPLC (reverse phase conditions), tR=6.82 min. MS (electrospray): m/z calculated for C21H26F3N3O3 [M++Na] 448.18, found 448.10. 1H NMR (CDCl3, 400 MHz): 7.73 (br d, J=8.2 Hz, 2H), 7.65 (br s, 2H), 4.64 (br s, 2H), 4.21 (t, J=6.4 Hz, 2H), 3.76 (br s, 2H), 3.66 (t, J=5.7 Hz, 2H), 2.73 (br t, J=5.4 Hz, 2H), 2.04 (q, J=6.1, 2H), 1.48 (s, 9H).

後処理

  1. stirringstirring
  2. waitcontinued for 17 h
  3. customThe mixture was partitioned between EtOAc (80 mL) and saturated aqueous NaHCO3 (20 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-03a75dfcb9e84a69a0d5053b6f86eaaf
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07388011B2

反応ノート

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