Hydrochloric Acid → Carbamic acid, [(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]-, 1,1-dimethylethyl ester

HRID 218990

반응식

HRID 218990 반응식
B.CSC.CB1N2CCC[C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[CH3:26][C:27]1([CH3:48])[O:32][C:31]2[CH:33]=[CH:34][C:35]([C:37](=[O:47])[CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:36][C:30]=2[CH2:29][O:28]1.Cl>C1COCC1.C1(C)C=CC=CC=1>[CH3:26][C:27]1([CH3:48])[O:32][C:31]2[CH:33]=[CH:34][C:35]([C@@H:37]([OH:47])[CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[CH:36][C:30]=2[CH2:29][O:28]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 10870948Carbamic acid, [2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxoethyl]-, 1,1-dimethylethyl esterHCID 12423031(Dimethyl sulfide)trihydroboron2회

생성물 1

HCID 10881838Carbamic acid, [(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]-, 1,1-dimethylethyl ester수율 85.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매3회

실험 절차

A 2M solution of borane-dimethyl sulphide in THF (28 ml) was added slowly to a 1M solution of (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole in toluene (56 ml) at 0° under nitrogen. A solution of tert-butyl 2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxoethylcarbamate, (108.2 g) in THF (1.3 liters) was added slowly keeping the temperature below 5° followed by 2M solution of borane-dimethyl sulphide in THF (252 ml) over 50 min. After 1 h, 2M HCl (170 ml) was added with cooling and the mixture was partitioned between EtOAc and water. The organic layer was washed with saturated NaHCO3 solution and brine and dried (MgSO4). The solution was concentrated and the product purified by chromatography on flash silica gel (800 g), eluting successively with hexane:EtOAc (4:1 then 3:1) to give the title compound (93.3 g), LCMS RT=3.31 min.

후처리

  1. customthe temperature below 5°
  2. temperaturewith cooling
  3. customthe mixture was partitioned between EtOAc and water
  4. washThe organic layer was washed with saturated NaHCO3 solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationThe solution was concentrated
  7. customthe product purified by chromatography on flash silica gel (800 g)
  8. washeluting successively with hexane:EtOAc (4:1

출처 및 근거

ORD 기록
ord-7ed40d96b05e4d4587185ba310ea6b8a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198483B2

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