Triphenylphosphine → 6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 2374447

反応式

HRID 2374447 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][OH:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][O:19][C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 59132278Tert-butyl 6-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

生成物 1

HCID 691462886-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester収率 49%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 6-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (85 mg, 0.323 mmol) in CH2Cl2 (1.5 mL) is added a solution of 4-chloro-3-trifluoromethyl-phenol (76 mg, 1.23 eq.) in CH2Cl2 (0.5 mL), PPh3 (127 mg, 1.5 eq.), and 1,1′-(azodicarbonyl)-dipiperidine (122 mg, 1.5 eq.). The mixture is stirred at room temperature overnight. All the solvent is removed under reduced pressure and the mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient) to give 70 mg of 6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

後処理

  1. customAll the solvent is removed under reduced pressure
  2. customthe mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient)

出典と根拠

ORDレコード
ord-bafc492e89c64c68b666ffba008967f7
出典データセット
uspto-grants-2008_12
特許番号
US07462629B2

関連ノート

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