Triphenylphosphine → HCID 18700148, 화합물

HRID 2289355노트

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HRID 2289355 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[C:4]([O:17][C:18]([F:21])([F:20])[F:19])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH:51](O)[CH2:50][CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH:51]([O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:12])[CH3:11])=[C:4]([O:17][C:18]([F:21])([F:19])[F:20])[CH:3]=2)[CH2:50][CH2:49]1)=[O:47])([CH3:44])([CH3:42])[CH3:43]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 18700104HCID 18700104, 화합물

생성물 1

HCID 18700148HCID 18700148, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a stirred solution of 4-hydroxy-1-(tert-butyldimethylsilyloxymethyl)-2-trifluoromethoxybenzene (3.2 g, 10 mmol) from Step 4 above and triphenylphosphine (3.9 g, 15 mmol) in THF (50 mL) at 0° C. was added a solution of N-tert-butyloxycarbonyl-4-piperidinol (3.0 g, 15 mmol) and DEAD (2.6 g, 15 mmol) in THF (25 mL) dropwise over a period of 1 h. The mixture was stirred at 0° C. for 3 h and then at ambient temperature for 12 h. The solvent was removed under reduced pressure and the residue was suspended in ether. The solid triphenylphosphine oxide was removed by filtration and the filtrate was purified by pressurized silica gel column chromatography using a gradient elution of 5-10% EtOAc:hexanes as eluant to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-1-(tert-butyldimethylsilyloxy-methyl)-2-trifluoromethoxybenzene as a colorless gum.

후처리

  1. waitat ambient temperature for 12 h
  2. customThe solvent was removed under reduced pressure
  3. customThe solid triphenylphosphine oxide was removed by filtration
  4. customthe filtrate was purified by pressurized silica gel column chromatography
  5. washa gradient elution of 5-10% EtOAc

출처 및 근거

ORD 기록
ord-65564d230cf84dac90c3fce118a828d9
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090805

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