(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane → tert-butyl (1S,4S)-5-[(5-nitro-1-benzofuran-7-yl)methyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 1162061Notes

Reaction equation

HRID 1162061 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[C@H:15]12[CH2:21][C@H:18]([NH:19][CH2:20]1)[CH2:17][N:16]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>>[N+:12]([C:5]1[CH:4]=[C:3]([CH2:2][N:19]2[CH2:20][C@@H:15]3[CH2:21][C@H:18]2[CH2:17][N:16]3[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 534029717-(Bromomethyl)-5-nitrobenzofuran2×

Product 1

HCID 66893419tert-butyl (1S,4S)-5-[(5-nitro-1-benzofuran-7-yl)methyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylateYield 79%

Procedure

The title compound was prepared according to the procedure of Example 112, Step 1, starting from 7-(bromomethyl)-5-nitro-1-benzofuran (120 mg, 70 mol %, 0.39 mmol; Intermediate 64) and tert-butyl (1S,4S)-(−)-2,5-diazabicyclo-(2.2.1)heptane-2-carboxylate (93 mg, 0.47 mmol). The title compound (115 mg, 79%) was obtained as a light yellow sticky oil. HPLC 99%, RT=2.34 min (System A; 5-60% MeCN over 3 min), 99%, RT=2.15 min (System B; 5-60% MeCN over 3 min). MS (ESI+) for C19H23N3O5 m/z 374 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-163c6169acc54e8aabe4e062bd4e5990
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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