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

HRID 2250364노트

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HRID 2250364 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

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온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-664b1f9e08424b888fba3e7d57d00609
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07317022B2

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