Ethanol → (R)-2-amino-2-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)propan-1-ol

HRID 1036447ノート

反応式

HRID 1036447 の反応式
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25]C(=O)[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].C(O)C.O>>[NH2:23][C@@:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([CH2:11][CH:8]3[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH2:9]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

参加物

5

反応物 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67415438(R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one

生成物 1

HCID 46196282(R)-2-amino-2-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)propan-1-ol収率 26.6%

実験手順

The mixture of (R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one (18.6 mg, 0.0000490 mol) and lithium hydroxide (12.9 mg, 0.000539 mol) in ethanol (1 mL, 0.02 mol) and water (0.50 mL, 0.028 mol) was heated to reflux overnight. The solvent was removed under vacuum and the residue was partitioned between water/CH2Cl2. The aqueous was extensively extracted with CH2Cl2 and the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into methylene chloride and subjected to chromatography with MeOH/CH2Cl2 (10:90 to 80:20) to give (R)-2-amino-2-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)propan-1-ol as a white solid (4.6 mg, 26%). LCMS: Rf=1.76 min 337.36 [M−NH2]+. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.88 (s, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.74 (d, J=7.0 Hz, 1H), 7.56 (s, 1H), 7.52 (dd, J=1.8, 8.7 Hz, 1H), 7.32 (d, J=8.3 Hz, 1H), 3.82-3.75 (m, 1H), 3.72-3.67 (m, 1H), 2.80 (d, J=8.0 Hz, 2H), 2.69 (br. s., 1H), 2.08 (br. s., 1H), 1.64 (d, J=12.9 Hz, 2H), 1.56 (br. s., 5H), 1.46 (tt, J=4.0, 13.0 Hz, 2H), 1.38-1.24 (m, 2H), 1.03 (tt, J=3.1, 11.9 Hz, 1H), 0.91 (s, 9H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed under vacuum
  4. customthe residue was partitioned between water/CH2Cl2
  5. extractionThe aqueous was extensively extracted with CH2Cl2
  6. dry with materialthe combined organic phase was dried over Na2SO4

出典と根拠

ORDレコード
ord-3f5b0e46e30146e59b501b2beb591f68
出典データセット
uspto-grants-2013_10
特許番号
US08546359B2

反応ノート

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