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

HRID 13223

반응식

HRID 13223 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-67a5a537560240f09f61349ff310076a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728030B2

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