(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (r)-8-Bromo-7-fluoro-4-methyl-3,4-dihydro-1h-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester

HRID 1760607Notes

Reaction equation

HRID 1760607 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([CH:12](C(C)(C)C(C)C)O[SiH](C)C)=[CH:5]2.[C:23]([O:27][C:28]([N:30]1[CH2:34][C@H:33]([CH3:35])OS1(=O)=O)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([N:30]1[CH2:34][C@@H:33]([CH3:35])[N:7]2[C:8]3[CH:9]=[C:10]([F:11])[C:2]([Br:1])=[CH:3][C:4]=3[CH:5]=[C:6]2[CH2:12]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 178444206HCID 178444206, compound

Product 1

HCID 68889795(r)-8-Bromo-7-fluoro-4-methyl-3,4-dihydro-1h-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester

Procedure

The title compound, ISP-MS: m/e=383.2 ([M+H]+) and m.p. 116-118° C., was prepared in accordance with the general method of example 26b) and c) from 5-bromo-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-6-fluoro-1H-indole and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-1f64bad27df5466492dbe1cab3e61c84
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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