1-Piperidinecarboxaldehyde → 10-Benzyl-3,7-dimethoxy-6-(tert.-butyl-dimethyl-silanyloxymethyl)phenothiazine-4-carbaldehyde

HRID 2395184ノート

反応式

HRID 2395184 の反応式
[CH2:1]([N:8]1[C:21]2[CH:20]=[CH:19][C:18]([O:22][CH3:23])=[C:17]([C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:33][CH3:34])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:40](N1CCCCC1)=[O:41]>C(OCC)C.O1CCCC1>[CH2:1]([N:8]1[C:9]2[CH:10]=[CH:11][C:12]([O:33][CH3:34])=[C:13]([CH:40]=[O:41])[C:14]=2[S:15][C:16]2[C:21]1=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=2[C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:28])([CH3:29])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 174291-PiperidinecarboxaldehydeHCID 178418339ButyllithiumHCID 178487334HCID 178487334、化合物

生成物 1

HCID 13732906710-Benzyl-3,7-dimethoxy-6-(tert.-butyl-dimethyl-silanyloxymethyl)phenothiazine-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 21868444Ether tetrahydrofuran溶媒

実験手順

A solution of 4.93 g (10.0 mmol) of 10-benzyl-4-(tert.-butyl-dimethyl-silanyloxymethyl)-3,7-dimethoxy-phenothiazine in 50 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 7.5 ml of n-butyllithium solution (1.6M in hexane) and 1.47 g (13.0 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The 10-benzyl-3,7-dimethoxy-6-(tert.-butyl-dimethyl-silanyloxymethyl)phenothiazine-4-carbaldehyde obtained was dissolved in 50 ml of tetrahydrofuran and reduced with 10.0 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.8.b. The reaction mixture was worked up and chromatographed analogously to that described in 4.1.1.ea. After drying in a high vacuum 3.72 g (71.9%) of 10-benzyl-6-(tert.-butyl-dimethyl-silanyloxymethyl)-3,7-dimethoxy-phenothiazin-4-yl-methanol were obtained as an amorphous white solid. MS:

出典と根拠

ORDレコード
ord-a74cc2516c6642d3a85bb4ff9523aea0
出典データセット
uspto-grants-1998_09
特許番号
US05811548

反応ノート

読み込み中…