1,2-Dichloroethane → 1-Tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine

HRID 1162828ノート

反応式

HRID 1162828 の反応式
[C:1]([N:8]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C[C:25]2[N:30]([OH:31])N=NC=2C=1.[CH2:32](Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[C:4]([O:3][C:1]([N:8]1[C@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C@@H:9]1[C:10]([N:30]([O:31][CH3:32])[CH3:25])=[O:12])=[O:2])([CH3:5])([CH3:6])[CH3:7]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2755972(2S,5R)-1-[(tert-butoxy)carbonyl]-5-phenylpyrrolidine-2-carboxylic acid

生成物 1

HCID 866174771-Tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of racemic N-Boc-cis-5-phenylproline (2 g, 6.865 mmol) in DMF (35 mL) was added HOBt (1.05 g, 6.87 mmol), EDC (1.97 g, 10.3 mmol), O, N-dimethylhydroxylamine hydrochloride (1.00 g, 10.3 mmol) and DIEA dropwise (1.33 mL, 10.3 mmol). The reaction was stirred at ambient temperature for 30 min and then partitioned between ethyl acetate and water. The EtOAc layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 50:50 ethyl acetate and hexane. Collection and concentration of appropriate fractions provided the title compound. HPLC RT=3.46 min, 86% at 215 nm (Method A); ES MS (M+H)=335.3.

後処理

  1. custompartitioned between ethyl acetate and water
  2. customThe EtOAc layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

出典と根拠

ORDレコード
ord-ef74f34f04034cfabecba5040835f3cc
出典データセット
uspto-grants-2010_10
特許番号
US07820680B2

反応ノート

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