N-Boc-2,5-diazabicyclo[2.2.1]heptane → 5-{(1R)-2-[(1R,4R)-2,5-Diazabicyclo[2.2.1]hept-2-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1 (3H)-one

HRID 2281328Notes

Reaction equation

HRID 2281328 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C@@H:12]1[CH2:14][O:13]1.[C@@H:15]12[CH2:21][C@@H:18]([NH:19][CH2:20]1)[CH2:17][N:16]2C(OC(C)(C)C)=O>>[C@@H:15]12[CH2:21][C@@H:18]([NH:19][CH2:20]1)[CH2:17][N:16]2[CH2:14][C@@H:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])[OH:13]

Participants

3

Reactant 2

HCID 11860399N-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×

Product 1

HCID 1176421475-{(1R)-2-[(1R,4R)-2,5-Diazabicyclo[2.2.1]hept-2-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1 (3H)-one

Procedure

5-{(1R)-2-[(1R,4R)-2,5-Diazabicyclo[2.2.1]hept-2-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1 (3H)-one was prepared in an analogous fashion as described for the synthesis of INTERMEDIATE 3 starting from 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1 (3H)-one (INTERMEDIATE 2) and commercially available tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate.

Sources & evidence

ORD record
ord-a1cba4ca97c14aa0ab4782ec29a14dc8
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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