Ethanol → HCID 67531512, compound

HRID 2389091Notes

Reaction equation

HRID 2389091 reaction equation
[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C@:19]1([CH3:25])[CH2:23][O:22]C(=O)[NH:20]1)[CH:13]=[CH:12]2.C(O)C.O.[OH-].[Li+].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][C@@H:2]3[CH2:3][C@@H:4]4[CH2:7][C@H:1]3[CH2:6][CH2:5]4)[CH:10]=2)[CH:15]=1)([CH3:25])[CH2:23][OH:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67530355HCID 67530355, compound

Product 1

HCID 67531512HCID 67531512, compoundYield 34.3%

Procedure

The compound was prepared in a manner similar as to that described (R)-4-(6-((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (100 mg, 0.0003 mol), ethanol (2.2 g, 0.049 mol), 4.2 M lithium hydroxide, monohydrate in water (2.1 mL, 0.0090 mol) to give 32 mg of the desired product as a white solid (32%). ESI-MS: 339 (M-16)+. 1H NMR (400 MHz, CDCl3) δ=7.94-7.61 (m, 3 H), 7.50 (d, J=8.5 Hz, 1 H), 7.23-7.05 (m, 2 H), 4.33-4.17 (m, 1 H), 3.84-3.51 (m, 2 H), 2.49-0.78 (m, 13 H).

Sources & evidence

ORD record
ord-7809b7e995aa45d1b4d6aa45b420aa25
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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