4-tert-Butylcyclohexanol → HCID 178445731, compound

HRID 2389161Notes

Reaction equation

HRID 2389161 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.O1CCCC1.[C:24]([CH:28]1[CH2:33][CH2:32][CH:31](O)[CH2:30][CH2:29]1)([CH3:27])([CH3:26])[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:24]([C@H:28]1[CH2:33][CH2:32][C@H:31]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)[CH2:30][CH2:29]1)([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 5

HCID 73914-tert-ButylcyclohexanolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 178445731HCID 178445731, compoundYield 64.5%

Procedure

(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (2.0460 g, 0.0084108 mol) was dissolved in tetrahydrofuran (20 mL, 0.2 mol) in a 100 mL RBF equipped with a magnetic stir bar. 4-tert-Butyl-cyclohexanol (1.58 g, 0.0101 mol) was added, followed by triphenylphosphine (3.53 g, 0.0134 mol) and the mixture was stirred for a few minutes. Diisopropyl azodicarboxylate (2.65 mL, 0.0134 mol) was then slowly added and the mixture was stirred overnight at room temperature. The mixture was concentrated under reduced pressure. The resulting product was adsorbed to silica gel and purified by flash chromatography (0-55% EtOAc in hexanes) to give 2.07 g of the title compound (64% yield). MS: m/z=382.23 [M+1] 1H NMR (MeOD) δ: 7.77-7.85 (m, 3H), 7.48 (dd, J=8.5, 2.0 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.16 (dd, J=8.8, 2.5 Hz, 1H), 4.49-4.54 (m, 1H), 4.41-4.46 (m, 1H), 4.32-4.41 (m, 1H), 2.25-2.35 (m, 2H), 1.94 (d, J=13.3 Hz, 2H), 1.81 (s, 3H), 1.38-1.52 (m, 2H), 1.16 (d, J=11.8 Hz, 2H), 0.92-0.98 (m, 9H)

Workup

  1. customRBF equipped with a magnetic stir bar
  2. stirringthe mixture was stirred overnight at room temperature
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified by flash chromatography (0-55% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d9afcc3777e5402dae7c3caf2a46f8bb
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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