4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → (S)-tert-Butyl 4-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 2175860Notes

Reaction equation

HRID 2175860 reaction equation
CC1C2COC(=O)C=2C=CC=1[C@@H]1CO1.[OH:15][CH:16]([C:33]1[C:34]([CH3:43])=[C:35]2[C:39](=[CH:40][CH:41]=1)[C:38](=[O:42])[O:37][CH2:36]2)[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C@H:19]1[CH2:31][OH:32]>>[OH:15][C@H:16]([C:33]1[C:34]([CH3:43])=[C:35]2[C:39](=[CH:40][CH:41]=1)[C:38](=[O:42])[O:37][CH2:36]2)[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][C@H:19]1[CH2:31][OH:32]

Participants

3

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 71270662(S)-tert-butyl 4-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Product 1

HCID 86727078(S)-tert-Butyl 4-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Procedure

(S)-tert-Butyl 4-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate was prepared starting from 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one in an analogous fashion to that described above for the synthesis of (S)-tert-butyl 4-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate.

Sources & evidence

ORD record
ord-4d139f3fcb344da7a49f11e5c0eb7885
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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