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

HRID 2389060Notes

Reaction equation

HRID 2389060 reaction equation
[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][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:21][CH2:20]4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.C(O)C.O.[OH-].[Li+]>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[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24]3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 67413569(R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

Product 1

HCID 46196192(R)-2-amino-2-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)propan-1-olYield 136.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one (0.3672 g, 0.0009284 mol) was dissolved in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL EPA vial equipped with a stir bar. 4.2 M Lithium hydroxide, monohydrate in water (2.00 mL) was added and the mixture was heated at 80° C. overnight. TLC analysis showed that the reaction was complete. The mixture was concentrated to dryness under vacuum. The product was dissolved in methylene chloride (5 mL) and washed with water (2×5 mL). The layers were separated (phase separator cartridge) and the organic layer was concentrated to dryness and purified by HPLC to give 0.467 g of the title compound (14% yield). MS: m/z=353.36 [M-NH2]+. 1H NMR (400 MHz, MeOD) δ 0.90-0.98 (m, 3 H), 1.10-1.24 (m, 1 H), 1.26-1.54 (m, 8 H), 1.58-1.74 (m, 2 H), 1.80 (s, 3 H), 1.86-1.95 (m, 2 H), 2.03-2.13 (m, 2 H), 2.20-2.29 (m, 2 H), 3.80-3.87 (m, 1 H), 3.91-3.97 (m, 1 H), 4.36-4.79 (m, 1 H, 1:1 ratio), 7.17-7.26 (m, 1 H, 1:1 ratio), 7.28 (d, J=2.51 Hz, 1 H), 7.53 (dd, J=8.78, 2.01 Hz, 1 H), 7.80-7.90 (m, 3 H)

Workup

  1. customvial equipped with a stir bar
  2. concentrationThe mixture was concentrated to dryness under vacuum
  3. dissolutionThe product was dissolved in methylene chloride (5 mL)
  4. washwashed with water (2×5 mL)
  5. customThe layers were separated (phase separator cartridge)
  6. concentrationthe organic layer was concentrated to dryness
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-fb3b3e11961d4f8b80c34f5b40ee2f1e
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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