Vinyl Acetate → (lR,3S)-(+)-3-tert-butyldimethylsilyloxycyclopentanyl acetate

HRID 2566

반응식

HRID 2566 반응식
[Si:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22](OC=C)(=[O:24])[CH3:23]>COC(C)(C)C>[C:22]([O:14][C@@H:11]1[CH2:12][CH2:13][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10]1)(=[O:24])[CH3:23]

참가 물질

5

반응물 3

HCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 54118351(1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-ol

생성물 1

HCID 54211622(lR,3S)-(+)-3-tert-butyldimethylsilyloxycyclopentanyl acetate수율 49%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

Combine (+/-)-cis-3-tert-butyldimethylsilyloxycyclopentanol (2.119 g, 9.8 mmol, prepared in example 29), pancreatin (6.2 g, 3 weight equivalents), triethylamine (0.9 mL, 6.5 mmol) and vinyl acetate (4.3 mL) in tert-butyl methyl ether (12 mL) and stir for 27 hours at room temperature. Then filter the reaction through diatomaceous earth and concentrate the filtrate under vacuum (room temperature/15 mmHg). Purify the residue by column chromatography [silica gel, 55 g, hexane (300 mL) followed by 5% ethyl acetate/hexane (500 mL)] to provide the (1R,3S)-(+)-3-tert-butyldimethylsilyloxycyclopentanyl acetate (1.23 g, 49% yield, 98% ee as determined from gas chromatography with a chiral column) and (1S,3R)-(-)-3-tert-butyldimethylsilyloxycyclopentanol (771 mg, 37% yield, 92% ee as determined from its acetate derivative followed by GC chiral column analysis, see example 30a).

후처리

  1. filtrationThen filter
  2. customthe reaction through diatomaceous earth
  3. concentrationconcentrate the filtrate under vacuum (room temperature/15 mmHg)
  4. customPurify the residue by column chromatography [silica gel, 55 g, hexane (300 mL) followed by 5% ethyl acetate/hexane (500 mL)]

출처 및 근거

ORD 기록
ord-b1dad0bf641048d099cfa0228402d3a6
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728899

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