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

HRID 1036410

Reaction equation

HRID 1036410 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-19785f35912243d49ad3902c1cce695b
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Linked notes

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