Ethanol → (2R)-2-amino-2-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)propan-1-ol

反応式

[CH3:1][C@@:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH:19]4[CH2:24][CH2:23][C:22]5([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]5)[CH2:21][CH2:20]4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.[OH-].[Li+].C(O)C.O>>[NH2:3][C@@:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH:19]3[CH2:24][CH2:23][C:22]4([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:21][CH2:20]3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]

参加物

反応物 4

HCID 702Ethanol

HCID 962Water

HCID 3939Lithium Hydroxide

HCID 67414094(4R)-4-methyl-4-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)oxazolidin-2-one

生成物 1

HCID 67415580(2R)-2-amino-2-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)propan-1-ol収率 31.2%

実験手順

The mixture of (4R)-4-methyl-4-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)oxazolidin-2-one (324 mg, 0.000823 mol) and lithium hydroxide (294 mg, 0.0123 mol) in ethanol (7.1 mL, 0.12 mol) and water (2.4 mL, 0.13 mol) was heated to reflux for 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 purification with MeOH/CH2Cl2 (10:90 to 80:20) to give the product (2R)-2-amino-2-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)propan-1-ol as a white powder (94.5 mg, 31.2%). LCMS Rf=1.70 min 351.34 ([M−NH2]+, 100%). 1H NMR (400 MHz, MeOD) δ=7.86 (d, J=1.6 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.74 (d, J=8.8 Hz, 1H), 7.57 (dd, J=2.0, 8.7 Hz, 1H), 7.22 (d, J=2.1 Hz, 1H), 7.14 (dd, J=2.4, 8.9 Hz, 1H), 4.53-4.44 (m, 1H), 3.75 (d, J=11.0 Hz, 1H), 3.70 (d, J=11.0 Hz, 1H), 2.01-1.88 (m, 2H), 1.80-1.65 (m, 4H), 1.55 (s, 3H), 1.50 (m, 8H), 1.42-1.30 (m, 4H).