1-Piperidinecarboxaldehyde → 10-Benzyl-3,7-dimethoxy-6-(tert.-butyl-dimethyl-silanyloxymethyl)phenothiazine-4-carbaldehyde
Reaction equation
[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]=1Participants
Procedure
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:
Sources & evidence
- ORD record
- ord-a74cc2516c6642d3a85bb4ff9523aea0
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811548
Reaction notes
Loading…