Sodium Hydroxide → 1-[(R)-tetrahydro-2-furoyl]-4-Boc-piperazine

HRID 2250364ノート

反応式

HRID 2250364 の反応式
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([OH:8])=O.S(Cl)(Cl)=O.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([N:23]1[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]1)=[O:8]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2734707Tetrahydro-2-furoic acid, (+)-

生成物 1

HCID 668793671-[(R)-tetrahydro-2-furoyl]-4-Boc-piperazine収率 80.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of (R)-tetrahydro-2-furoic acid (5 g, 43.06 mmol) in toluene (75 mL) was added thionyl chloride (7.68 g, 64.6 mmol). The mixture was stirred at 90° C. for 2 h, then slowly cooled to 0° C. To a separate flask was charged a solution of N-Boc piperazine (8.02 g, 43.06 mmol) in toluene (40 mL), and aqueous sodium hydroxide (10.3 g, 258 mmol) in water (80 mL). This biphasic solution was cooled in an ice bath, followed by the addition of the cold acid chloride prepared above. The mixture was stirred vigorously for 2 h. The organic phase was collected, and washed with 1M H3PO4, dried and evaporated, to provide the title intermediate (9.87 g).

後処理

  1. temperatureslowly cooled to 0° C
  2. temperatureThis biphasic solution was cooled in an ice bath
  3. customprepared above
  4. stirringThe mixture was stirred vigorously for 2 h
  5. customThe organic phase was collected
  6. washwashed with 1M H3PO4
  7. customdried
  8. customevaporated

出典と根拠

ORDレコード
ord-664b1f9e08424b888fba3e7d57d00609
出典データセット
uspto-grants-2008_01
特許番号
US07317022B2

反応ノート

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