Isopropanol → t-Butyl (1R,2R)-1-(2,3-dihydrobenzofuran-6-yl)-1-hydroxypropan-2-ylcarbamate

HRID 1098992

Reaktionsgleichung

Reaktionsgleichung von HRID 1098992
[O:1]1[C:5]2[CH:6]=[C:7]([C:10](=[O:21])[C@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CC(O)C.[Al](OC(C)C)(OC(C)C)OC(C)C>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[C:7]([C@@H:10]([OH:21])[C@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH3:12])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 16685055Aluminum tri-iso-propoxideHCID 59339724(R)-t-butyl 1-(2,3-dihydrobenzofuran-6-yl)-1-oxopropan-2-ylcarbamate

Produkt 1

HCID 59339796t-Butyl (1R,2R)-1-(2,3-dihydrobenzofuran-6-yl)-1-hydroxypropan-2-ylcarbamateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(R)-t-butyl 1-(2,3-dihydrobenzofuran-6-yl)-1-oxopropan-2-ylcarbamate (306d, 2.21 g, 7.59 mmol) was dissolved in propan-2-ol (6.35 mL, 83.4 mmol) and toluene (10 mL). Al(OiPr)3 (0.310 g, 1.52 mmol) was added, and the reaction vessel was capped and flushed with argon. The mixture was stirred at 50° C. overnight. Then another portion of Al(OiPr)3 (330 mg) was added, and stirring was continued for 5 h. The mixture was cooled to r.t., and partitioned between aq. HCl (1N, 25 ml) and ethyl acetate (80 ml). The organic layer was separated and dried. The solvent was removed in vacuo and purified by flash chromatography on silica gel with n-heptane/ethyl acetate (6:4) to give 1.58 g (71%) of subtitle compound.

Aufarbeitung

  1. customthe reaction vessel was capped
  2. customflushed with argon
  3. additionThen another portion of Al(OiPr)3 (330 mg) was added
  4. stirringstirring
  5. waitwas continued for 5 h
  6. temperatureThe mixture was cooled to r.t.
  7. custompartitioned between aq. HCl (1N, 25 ml) and ethyl acetate (80 ml)
  8. customThe organic layer was separated
  9. customdried
  10. customThe solvent was removed in vacuo
  11. custompurified by flash chromatography on silica gel with n-heptane/ethyl acetate (6:4)

Quellen und Nachweise

ORD-Eintrag
ord-92ee1f8690cb43a8be30e7a3f0a87537
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

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