Ethanol → (R)-2-amino-2-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)propan-1-ol

HRID 2389070Notes

Reaction equation

HRID 2389070 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([C@:19]2([CH3:25])[CH2:23][O:22]C(=O)[NH:20]2)[CH:13]=[CH:12]3)[CH2:4][CH2:3]1.[OH-].[Li+].C(O)C.O>>[NH2:20][C@@:19]([C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH:5]3[CH2:6][CH2:7][C:2]([CH3:26])([CH3:1])[CH2:3][CH2:4]3)[CH:10]=2)[CH:15]=1)([CH3:25])[CH2:23][OH:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67414756(R)-4-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 46196208(R)-2-amino-2-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)propan-1-ol

Procedure

The mixture of (R)-4-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one and lithium hydroxide (45 mg, 0.0019 mol) in ethanol (1.1 mL, 0.019 mol) and water (0.37 mL, 0.021 mol) was heated to reflux for overnight. The crude product was partitioned between ethyl acetate and water and the ethyl acetate layer was concentrated and the crude was brought up in methanol and purified by HPLC. MS: m/z=311.2 [M-NH2]+

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. customThe crude product was partitioned between ethyl acetate and water
  4. concentrationthe ethyl acetate layer was concentrated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-f0da6869cbfb456e9b9cb017735ff069
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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