Methanol → (2R)-2-[(Triphenylmethyl)amino]butan-1-ol

HRID 1432387

反応式

HRID 1432387 の反応式
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCCCCC.CO>C(Cl)Cl>[C:7]([NH:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 887MethanolHCID 6456Trityl chlorideHCID 8058HexaneHCID 27238562-Amino-1-butanol, (-)-

生成物 1

HCID 57395035(2R)-2-[(Triphenylmethyl)amino]butan-1-ol収率 86.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (R)-(−)-2-aminobutan-1-ol (10 g, 112.18 mmol) in CH2Cl2 (500 mL) under Ar at RT, was added Pri2NEt (30 mL, 172.22 mmol) followed by trityl chloride (35.4 mL, 126.98 mmol). The reaction mixture was stirred at RT for 48 h, when TLC (55:40:5 hexane/Et20/MeOH) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue precipitated from Me2CO (50 mL) with hexane (900 mL) with stirring, the precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in hexane (1 L), filtered, and the filtrate was evaporated in vacuo to afford the title compound as a light yellow oil (32 g, 86%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.56 (t, 3H, J=7.41, —NHCH(CH2CH3)CH2OH), 1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.21 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.72+3.00 (2×m, 2H, —NHCH(CH2CH3)CH2OH), 4.28 (t, 1H, J=5.26 Hz, —NHCH(CH2CH3)CH2OH), 7.14-7.49 (m, 15H, 3×Bz).

後処理

  1. customThe solvent was evaporated in vacuo
  2. customthe residue precipitated from Me2CO (50 mL) with hexane (900 mL)
  3. stirringwith stirring
  4. customthe precipitate was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionThe residue was dissolved in hexane (1 L)
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-2d0a4f561e684b1fb0a8ceacb975eba2
出典データセット
uspto-grants-2009_11
特許番号
US07612079B2

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