Ethanol → 4-[Bromo-(4-ethoxycarbonylamino-phenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 2120903노트

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HRID 2120903 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18](C(O)=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[CH2:49]([OH:51])[CH3:50]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18]([NH:44][C:47]([O:51][CH2:49][CH3:50])=[O:32])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 702EthanolHCID 8471Triethylamine2회HCID 199401P,P-Diphenylphosphinic azideHCID 10834544HCID 10834544, 화합물

생성물 1

HCID 692435694-[Bromo-(4-ethoxycarbonylamino-phenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
95 °C

실험 절차

To a mixture of compound 51, prepared according to Scheme 6, (0.25 g, 0.625 mmole) in toluene (5 mL), was added diphenylphosphorylazide (0.192 g, 0.70 mmole) and triethylamine (0.1 mL, 0.7 mmole). After stirring the mixture under argon at 95° C. for two hours an excess of anhydrous ethanol (2 mL) and triethylamine (0.1 mL) were added and the solution was stirred at 95° C. for an additional 5 hours. After cooling to room temperature the reaction mixture was partitioned between water and diethyl ether. The ether was washed with water, dried over magnesium sulfate and removed in vacuo to give the product (compound 88) as a tan foam (300 mg, 99% yield).

후처리

  1. customprepared
  2. additionwere added
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. customwas partitioned between water and diethyl ether
  5. washThe ether was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customremoved in vacuo

출처 및 근거

ORD 기록
ord-67cf9ed921eb4c6794379c5365d0bbb5
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693117B2

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