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

HRID 1098992

反応式

HRID 1098992 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-92ee1f8690cb43a8be30e7a3f0a87537
出典データセット
uspto-grants-2012_03
特許番号
US08143290B2

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