2-Vinylnaphthalene → (R)-(2-Hydroxy-1-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester

HRID 1825043Notes

Reaction equation

HRID 1825043 reaction equation
[OH-].[Na+].[C:3](=[O:10])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[NH2:4].Cl[O:12]C(C)(C)C.[CH:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)=[CH2:18]>O.C(O)CC.O.O.[Os](=O)(=O)=O.[K].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1>[C:6]([O:5][C:3](=[O:10])[NH:4][C@H:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)[CH2:18][OH:12])([CH3:9])([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 132302-VinylnaphthaleneHCID 14798Sodium Hydroxide2×HCID 77922tert-Butyl carbamateHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 57419701(R)-(2-Hydroxy-1-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl esterYield 56.6%

Reagents, catalysts & solvents 4

HCID 112172021,4-Bis(dihydroquinidine)phthalazineCatalystHCID 178526964HCID 178526964, compoundCatalyst2×HCID 962WaterSolventHCID 10311-PropanolSolvent3×

Procedure

Sodium hydroxide (1.89 g, 16 mmol) was dissolved in water (115 mL) and 5.4 mL of this solution was used to dissolve potassium osmium (VI) oxide dihydrate (240 mg) to get a purple suspension. The rest of the sodium hydroxide solution was treated with t-butyl carbamate (5.580 g, 47.1 mmol) in n-propanol (54 mL), followed by addition of t-butyl hypochlorite (5.4 mL, 47.1 mmol). This solution was stirred for 5 min, then hydroquinidine 1,4-phthalazinediyl diether (630 mg) in n-propanol (54 mL) was added, followed by a solution of 2-vinylnaphthalene (2.5 g, 16 mmol) in n-propanol (54 mL) and a solution of potassium osmium (VI) oxide dihydrate previously made. The reaction mixture was stirred at room temperature for 0.5 hr. The reaction mixture was quenched with saturated NaHSO3 solution. After concentration, the residue was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, concentrated under vacuum. The crude product was purified by flash chromatography with 20% ethyl acetate in hexanes to give the title compound (2.6 g) as a solid.

Workup

  1. customto get a purple suspension
  2. stirringThe reaction mixture was stirred at room temperature for 0.5 hr
  3. customThe reaction mixture was quenched with saturated NaHSO3 solution
  4. concentrationAfter concentration
  5. extractionthe residue was extracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by flash chromatography with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cf6fbb6d72ab417ba121cfa20020944f
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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