Trifluoroacetic acid → (3RS,4S)-4-Amino-2-methyl-hexan-3-ol

HRID 81439ノート

反応式

HRID 81439 の反応式
[CH3:1][CH:2]([CH:4]([OH:28])[C@@H:5]([NH:8]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][CH3:7])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@@H:5]([CH2:6][CH3:7])[CH:4]([OH:28])[CH:2]([CH3:3])[CH3:1]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 57714148(3RS,4S)-2-methyl-4-(trityl-amino)-hexan-3-ol

生成物 1

HCID 57714157(3RS,4S)-4-Amino-2-methyl-hexan-3-ol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (3RS,4S)-2-methyl-4-(trityl-amino)-hexan-3-ol (0.36 g, 1 eq, 0.97 mmol) in DCM (20 mL) under an argon atmosphere at room temperature, was added CF3COOH (5 mL) dropwise, and the solution was stirred at this temperature for 1 h. The solvent was evaporated in vacuo, the residue was precipitated from Et2O (10 mL) with hexane (90 mL) with stirring to give a yellow oil. The solvent was decanted from the oil, and the oil was washed with hexane (20 mL) and dried in vacuo to afford the title compound as a light yellow oil. Yield: 0.13 g (100%). (50% de 3R,4S: 50% de 3S,4S) 1H-NMR (d6-DMSO, 250 MHz): δ 0.85-1.01 (m, 9H, NH2CH (CH2CH3)CH(CH(CH3)2OH), 1.44-1.76 (m, 2H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 2.94 (m, 1H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 3.17 (m, 1H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 3.40 (m, 1H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 7.54 (bs, 2H, NH2CH(CH2CH3)CH(CH(CH3)2)OH).

後処理

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was precipitated from Et2O (10 mL) with hexane (90 mL)
  3. stirringwith stirring
  4. customto give a yellow oil
  5. customThe solvent was decanted from the oil
  6. washthe oil was washed with hexane (20 mL)
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-8aa3a37cb8254f8b8f3e702c03a408ea
出典データセット
uspto-grants-2014_09
特許番号
US08846696B2

反応ノート

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