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

HRID 2566

反応式

HRID 2566 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

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).

後処理

  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)]

出典と根拠

ORDレコード
ord-b1dad0bf641048d099cfa0228402d3a6
出典データセット
uspto-grants-1998_03
特許番号
US05728899

関連ノート

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