Potassium Bicarbonate → tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate

HRID 582533ノート

反応式

HRID 582533 の反応式
[CH3:1][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([O:13]C=O)[CH2:9]1)([CH3:4])[CH3:3].C(=O)([O-])O.[K+]>CO.O.C(OCC)(=O)C>[CH3:4][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)([CH3:1])[CH3:3]

参加物

6

反応物 2

HCID 516893Potassium BicarbonateHCID 86754023(1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentyl formate

生成物 1

HCID 21637082tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate収率 52.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83-85° C., [α]D 0.0° (CHCl3 c=0.55%).

後処理

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. customevaporated
  4. customto leave a solid which
  5. customwas purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-5c6b4d35a75f46c08faf4e9123193d33
出典データセット
uspto-grants-1999_07
特許番号
US05925624

反応ノート

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