Hydrochloric Acid → 4-[(1S,4S)-2,5-Diazabicyclo[2.2.1]hept-2-ylmethyl]phenol Dihydrochloride

HRID 1807455Notes

Reaction equation

HRID 1807455 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][C@@H:11]3[CH2:13][C@H:8]2[CH2:9][N:10]3C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.[ClH:23]>C(Cl)Cl>[ClH:23].[ClH:23].[C@H:8]12[CH2:13][C@H:11]([NH:10][CH2:9]1)[CH2:12][N:7]2[CH2:6][C:5]1[CH:21]=[CH:22][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57514842tert-Butyl (1S,4S)-5-(4-hydroxybenzyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 574640624-[(1S,4S)-2,5-Diazabicyclo[2.2.1]hept-2-ylmethyl]phenol DihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1S,4S)-5-(4-hydroxybenzyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (3.47 g, 0.0114 mol, 1 equiv.) in CH2Cl2 (42 mL) was added HCl (4 M in dioxane, 22.5 mL, 0.114 mol, 10 equiv.). The solution was stirred at rt for 12 h. The mixture was then concentrated, affording a white solid (100%). 1H NMR (500 MHz, DMSO-d6): 11.60-11.28 (m, 1H), 10.38-9.95 (m, 1H), 9.93-9.56 (m, 2H), 7.49 (s, 2H), 6.81 (s, 2H), 4.39 (m, 4H), 3.88 (s, 1H), 3.67 (s, 1H), 2.72-2.52 (m, 0.5H), 2.45-2.30 (m, 0.5H), 2.08 (s, 1H). MS (ESI): mass calcd. for C12H16N2O, 204.27; m/z found, 205.1 [M+H]+.

Workup

  1. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-dbd5dc39ef174a4cb2c9dfb5b1253f66
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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