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Lithium borohydride → [3-Amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2':6',2'']terpyridin-1'-ylmethyl)-phenyl]-methanol

HRID 1987358
ノート
印刷プレビュー

反応式

HRID 1987358 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:16]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:6]([NH2:31])[CH:5]=1.[Li+].[BH4-]>C1COCC1.[OH-].[Na+]>[NH2:31][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[CH2:10][N:11]1[CH:12]([C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:13][CH2:14][CH2:15][CH:16]1[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 674211763-amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-benzoic acid methyl ester

生成物 1

HCID 67421957[3-Amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2':6',2'']terpyridin-1'-ylmethyl)-phenyl]-methanol収率 38.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 14798
Sodium Hydroxide
溶媒

実験手順

To a solution of 3-amino-4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (0.61 g, 1.42 mmol) in THF (14 mL) was added LiBH4 (430 mg, 19.74 mmol) and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, diluted with 1.0 N NaOH (20 mL) and extracted with CH2Cl2 (5×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.220 g (37%) of COMPOUND 59 as a white solid. 1H NMR (CDCl3) δ 1.23 (br s, 1H), 1.47-1.72 (m, 3H), 1.88-1.95 (m, 1H), 2.04-2.18 (m, 2H), 2.35 (s, 6H), 3.32 (s, 2H), 3.73 (dd, 2H, J=11.7, 3.0 Hz), 4.26 (d, 2H, J=3.3 Hz), 4.53 (br s, 2H), 6.03 (s, 1H), 6.07 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.2 Hz), 6.86 (dd, 2H, J=7.8, 4.8 Hz), 7.15 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz). 13C NMR (CDCl3) δ 19.44, 25.02, 32.92, 60.69, 65.60, 68.25, 112.98, 115.09, 122.09, 122.80, 129.96, 131.38, 138.18, 140.42, 146.89, 147.51, 161.18; ES-MS m/z 403 (M+H). Anal. Calcd. For C25H30N4O.1.0H2O: C, 71.40; H, 7.67; N, 13.32. Found: C, 71.31; H, 7.55; N, 13.22.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with CH2Cl2 (5×30 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH)

出典と根拠

ORDレコード
ord-b227d6cd32f047fdbe9e84a267f5725a
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07550484B2

反応ノート

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