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

HRID 2389108노트

반응식

HRID 2389108 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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, 1 H), 7.77 (d, J=8.0 Hz, 1 H), 7.74 (d, J=7.0 Hz, 1 H), 7.56 (s, 1 H), 7.52 (dd, J=1.8, 8.7 Hz, 1 H), 7.32 (d, J=8.3 Hz, 1 H), 3.82-3.75 (m, 1 H), 3.72-3.67 (m, 1 H), 2.80 (d, J=8.0 Hz, 2 H), 2.69 (br. s., 1 H), 2.08 (br. s., 1 H), 1.64 (d, J=12.9 Hz, 2 H), 1.56 (br. s., 5 H), 1.46 (tt, J=4.0, 13.0 Hz, 2 H), 1.38-1.24 (m, 2 H), 1.03 (tt, J=3.1, 11.9 Hz, 1 H), 0.91 (s, 9 H).

후처리

  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

출처 및 근거

ORD 기록
ord-5a090c1d85fb44d7960ae74cea76ea21
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269043B2

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