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

HRID 2374447

반응식

HRID 2374447 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-bafc492e89c64c68b666ffba008967f7
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462629B2

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