Trimethylamine oxide dihydrate → (2-Hydroxy-2-hydroxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-carbamic acid benzyl ester

HRID 1420798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420798
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH:12]1[CH2:17][CH:16]2[CH2:18][CH:14]([C:15]2([CH3:20])[CH3:19])[C:13]1=[CH2:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:23].[OH2:24].C[N+]([O-])(C)C>C(Cl)Cl.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH:12]1[CH2:17][CH:16]2[CH2:18][CH:14]([C:15]2([CH3:19])[CH3:20])[C:13]1([OH:24])[CH2:21][OH:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 198430Trimethylamine oxide dihydrateHCID 54031778(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-carbamic acid benzyl ester

Produkt 1

HCID 54267394(2-Hydroxy-2-hydroxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-carbamic acid benzyl esterAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-carbamic acid benzyl ester (2.19 g, 7.32 mmol), prepared in step B of example 47, was dissolved in CH2Cl2 (50 ml). To this solution was added trimethylamine N-oxide dihydrate (894 mg, 8.79 mmol) and osmium tetroxide (136 mg, 0.535 mmol). The solution was stirred at ambient temperature for 16 hours after which time the reaction was concentrated under vacuum and chromatographed on silica gel using a gradient starting with 30% ethyl acetate in hexanes to 50% ethyl acetate in hexanes to give 1.51 g of the titled compound as a brown oil: C.I. m/z 316 [M+1-H2 0]; 1H NMR (CDCl3)δ 7.31-7.39 (m, 5H), 5.59 (br s, 1H), 5.12 (s, 2H), 3.30-3.58 (m, 4H), 1.93-2.28 (m, 4H), 1.52 (m, 1H), 1.24-1.30 (m, 5H), 0.96 (s, 3H).

Aufarbeitung

  1. concentrationwas concentrated under vacuum
  2. customchromatographed on silica gel using a gradient

Quellen und Nachweise

ORD-Eintrag
ord-67255f7892c3480f81e17c548f411c9d
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071935

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