Sulfuric Acid → (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

HRID 1034528ノート

反応式

HRID 1034528 の反応式
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[C:17](OC)=[O:18])=[O:6])[CH:2]=[CH2:3].[BH4-].[Na+].S(=O)(=O)(O)O>O1CCCC1.C(O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 10733517(2S,4R)-N-allyloxycarbonyl-4-methanesulfonyloxyproline methyl ester

生成物 1

HCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol収率 93.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine (27.12 g: 74.0 mmole) in a mixture of tetrahydrofuran (94 ml) and ethanol (140 ml), sodium borohydride (12 g: 31.7 mmole) is added in a nitrogen atmosphere under ice cooling. The mixture is stirred for 4 hours at room temperature. To the reaction mixture concentrated sulfuric acid (8.8 ml: 158.4 mmole) is added dropwise under ice cooling. The reaction mixture is concentrated to half a volume in vacuo, and diluted with ethyl acetate (100 ml) and ice water (100 ml). The organic layer is taken, successively washed with aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated in vacuo to give (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (19.33 g). Yield: 77%. Colorless oil. NMR δ(CDCl3) ppm: 1.9 to 2.1(m, 1H), 2.3 to 2.5(m, 1H), 3.05(s, 3H), 3.5 to 3.7(m, 2H), 3.7 to 4.1(m, 2H), 4.1 to 4.3(m, 1H), 4.6(m, 2H), 5.2 to 5.4(m, 3H), 5.8 to 6.1(m, 1H).

後処理

  1. additionis added in a nitrogen atmosphere under ice cooling
  2. concentrationThe reaction mixture is concentrated to half a volume in vacuo
  3. additiondiluted with ethyl acetate (100 ml) and ice water (100 ml)
  4. washsuccessively washed with aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ff0cdf2580e84edc99121273787baf22
出典データセット
uspto-grants-1994_05
特許番号
US05317016

反応ノート

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