p-Toluenesulfonic acid → HCID 86018577、化合物

HRID 1455518ノート

反応式

HRID 1455518 の反応式
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([CH:7]=[O:8])[CH2:3]1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]=[O:8])[CH2:3]1

参加物

4

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 57948626HCID 57948626、化合物

生成物 1

HCID 86018577HCID 86018577、化合物収率 100%

実験手順

The (R)-3-hydroxypyrrolidine-1-carbaldehyde (31 g) was treated with dihydropyran (36.8 ml) and p-toluenesulphonic acid (1 g). The mixture was stirred at room temperature for approximately one hour, during which time the colour changed from yellow to dark purple. GC analysis showed the reaction was complete. The reaction was quenched by addition of saturated sodium bicarbonate solution (90 ml). The aqueous phase was extracted with DCM (3×90 ml). The combined organic phase was washed with saturated sodium chloride solution (90 ml), then dried over MgSO4 and concentrated at below 30° C. The product, 3-(tetrahydropyran-2-yloxy)pyrrolidine-1-carbaldehyde, was obtained in 100% yield, 54.5 g. GC analysis showed two adjacent peaks, RT 14.45 and 14.83 min, 49.7 and 47.1% respectively. δH (CDCl3) 8.22 and 8.27 (1H, 2×s), 4.60-4.75 (1H, m), 4.35-4.50 (1H, m), 3.80-3.95 (1H, m), 3.40-3.70 (5H, m), 1.40-2.20 (8H, m).

後処理

  1. customThe reaction was quenched by addition of saturated sodium bicarbonate solution (90 ml)
  2. extractionThe aqueous phase was extracted with DCM (3×90 ml)
  3. washThe combined organic phase was washed with saturated sodium chloride solution (90 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated at below 30° C

出典と根拠

ORDレコード
ord-83271084f9fc4da0ba46c20d775db933
出典データセット
uspto-grants-2009_01
特許番号
US07482452B2

反応ノート

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