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Boron trifluoride → 1-(4-Methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol

HRID 1363381
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HRID 1363381 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=3[O:25][CH3:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].B(F)(F)F.C1C[O:36]CC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=3[O:25][CH3:26])[CH:13]([OH:36])[CH2:14]2)=[CH:7][CH:8]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 6356Boron trifluorideHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 669341641,2,3,6-Tetrahydro-1-(4-methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)pyridine

생성물 1

HCID 669340611-(4-Methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol

반응 조건

온도
52.5 °C

실험 절차

Compound of example 118 (15 g, 42 mmol) was subjected to hydroboration using NaBH4 (2.7 g, 71.4 mmol) and BF3-etherate (12.6 g, 88.8 mmol) in THF (50 mL). Excess diborane was destroyed by the addition of water. Conc. HCl (15 mL) was added and the reaction mixture was stirred at 50-55° C. for 1 h. It was cooled to room temperature The resulting mixture was made basic (pH 12-14) using an aqueous 50% NaOH solution. 30% H2O2 (9 mL) was added and the reaction mixture was stirred at 50-55° C. for 1 h. The reaction mixture was processed as described in example 2 to obtain the title compound.

후처리

  1. customExcess diborane was destroyed by the addition of water
  2. additionConc. HCl (15 mL) was added
  3. temperatureIt was cooled to room temperature The resulting mixture
  4. addition30% H2O2 (9 mL) was added
  5. stirringthe reaction mixture was stirred at 50-55° C. for 1 h

출처 및 근거

ORD 기록
ord-fafe500061e3499aa8c1a6f20f626e11
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07884127B2

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