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

HRID 1825043노트

반응식

HRID 1825043 반응식
[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]

참가 물질

9

반응물 4

HCID 132302-VinylnaphthaleneHCID 14798Sodium Hydroxide2회HCID 77922tert-Butyl carbamateHCID 521297Tert-Butyl hypochlorite

생성물 1

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

시약·촉매·용매 4

HCID 112172021,4-Bis(dihydroquinidine)phthalazine촉매HCID 178526964HCID 178526964, 화합물촉매2회HCID 962Water용매HCID 10311-Propanol용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cf6fbb6d72ab417ba121cfa20020944f
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045551B2

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