Hydrochloric Acid → HCID 13042967、化合物

HRID 1371768ノート

反応式

HRID 1371768 の反応式
[CH3:1][S:2]([N:5]1[CH2:11][CH2:10][CH:9]2[CH:7]([O:8]2)[CH2:6]1)(=[O:4])=[O:3].[Br-:12].[Li+].Cl>O1CCCC1.[Cu](Br)Br>[Br:12][CH:9]1[CH2:10][CH2:11][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH:7]1[OH:8]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 82050Lithium BromideHCID 13042966HCID 13042966、化合物

生成物 1

HCID 13042967HCID 13042967、化合物

試薬・触媒・溶媒 2

HCID 24611Copper bromide (CuBr2)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of the epoxide (177 mg, 1 mmol, Example 303) in tetrahydrofuran (8 mL), lithium bromide (543 mg, 6.25 mmol, Aldrich) and copper(II)bromide (725 mg, 3.25 mmol, Aldrich) were added and the mixture was stirred at room temperature overnight. The mixture was poured into 0.1N hydrochloric acid (33 mL) and extracted with ethyl acetate (3×10 mL). The extracts were combined, washed with water, brine and dried with MgSO4. The solvent was removed to give the desired product as colorless oil after passing through an aluminum column (eluted with 5% methanol/dichloromethane). 237 mg, 92%. H1NMR (300 MHz, CDCl3), ppm: 2.00–2.20 (m), 1H; 2.38–2.52 (m), 1H; 2.70 (br), 1H (OH); 2.99 (s), 3H; 3.0–3.20 (m), 2H; 3.50–3.51 (m), 1H; 3.80–3.97 (m), 2H; 4.0–4.10 (m), 1H. The compound was used directly for the next step.

後処理

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washwashed with water, brine
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed

出典と根拠

ORDレコード
ord-7f726203748a4bcdb118a5ee1d2e07df
出典データセット
uspto-grants-2007_01
特許番号
US07157455B2

反応ノート

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