2-(Trimethylsilyl)ethyl chloroformate → beta-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-[4-(2-trimethylsilyl-ethoxymethoxy)-naphthalen-2-yl-methoxy]-piperidine-1-carboxylate

HRID 1004944Notes

Reaction equation

HRID 1004944 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][Si:7]([CH3:10])([CH3:9])[CH3:8])=[O:3].C([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:20]([O:31][CH2:32][C:33]2[CH:42]=[C:41]([O:43][CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=2)[CH2:19]1)C1C=CC=CC=1>>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH:21]2[CH2:22][CH2:23][N:18]([C:2]([O:4][CH2:5][CH2:6][Si:7]([CH3:10])([CH3:9])[CH3:8])=[O:3])[CH2:19][CH:20]2[O:31][CH2:32][C:33]2[CH:42]=[C:41]([O:43][CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 109101682-(Trimethylsilyl)ethyl chloroformateHCID 22127049(3RS,4RS)-1-benzyl-4-(4-fluoro-phenyl)-3-[4-(2-trimethylsilyl-ethoxymethoxy)-naphthalen-2-ylmethoxy]-piperidine

Product 1

HCID 86604391beta-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-[4-(2-trimethylsilyl-ethoxymethoxy)-naphthalen-2-yl-methoxy]-piperidine-1-carboxylate

Procedure

In an analogous manner to that described in Example 1(d) by cleavage of the benzyl group by means of β-trimethylsilylethyl chloroformate from (3RS,4RS)-1-benzyl-4-(4-fluoro-phenyl)-3-[4-(2-trimethylsilyl-ethoxymethoxy)-naphthalen-2-ylmethoxy]-piperidine there was obtained β-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-[4-(2-trimethylsilyl-ethoxymethoxy)-naphthalen-2-yl-methoxy]-piperidine-1-carboxylate as a light yellow oil; MS: 626 (M+H)+.

Sources & evidence

ORD record
ord-cf02768e96784d4497390a7b91c6807b
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

Loading…