Triphenylphosphine → HCID 18700148、化合物

HRID 2289355ノート

反応式

HRID 2289355 の反応式
[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]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 18700104HCID 18700104、化合物

生成物 1

HCID 18700148HCID 18700148、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65564d230cf84dac90c3fce118a828d9
出典データセット
uspto-grants-2000_07
特許番号
US06090805

反応ノート

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