2-(Trimethylsilyl)ethyl chloroformate → HCID 86604430, compound

HRID 1005080Notes

Reaction equation

HRID 1005080 reaction equation
C([N:8]1[CH2:13][CH:12]([CH2:14][CH2:15][CH3:16])[CH:11]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:10]([O:24][CH2:25][C:26]2[CH:35]=[C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH2:9]1)C1C=CC=CC=1.Cl[C:45]([O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])=[O:46]>>[CH2:37]([O:36][C:34]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH2:25][O:24][CH:10]2[CH:11]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH:12]([CH2:14][CH2:15][CH3:16])[CH2:13][N:8]([C:45]([O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])=[O:46])[CH2:9]2)[CH:35]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 109101682-(Trimethylsilyl)ethyl chloroformateHCID 22128736HCID 22128736, compound

Product 1

HCID 86604430HCID 86604430, compound

Procedure

In an analogous manner to that described in Example 1(d), by reacting (3RS,4RS,5SR)-1-benzyl-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(4-fluoro-phenyl)-5-propyl-piperidine with β-trimethylsilylethyl chloroformate [Synthesis 346 (1987)] there was obtained 2-trimethylsilanylethyl (3RS,4RS,5SR)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(4-fluoro-phenyl)-5-propyl-piperidine-1-carboxylate as a pale yellow syrup, MS: 628 (M+H)+.

Sources & evidence

ORD record
ord-e56aebe68a5d4925b93a1a69faa6b0ef
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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