4-Bromobenzyl bromide → tert-butyl-4-((1R,2R)-2-{[(4-bromobenzyl)oxy]methyl}cyclopropyl)piperidine-1-carboxylate

HRID 1468825Notes

Reaction equation

HRID 1468825 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@@H:4]1[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][CH:6]([C@H:4]2[CH2:5][C@H:3]2[CH2:2][O:1][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([Br:19])=[CH:21][CH:22]=2)[CH2:11][CH2:10]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 53393314HCID 53393314, compound2×

Product 1

HCID 86717781tert-butyl-4-((1R,2R)-2-{[(4-bromobenzyl)oxy]methyl}cyclopropyl)piperidine-1-carboxylate

Procedure

Using the conditions outlined in intermediate 5 (step C) tert-butyl 4-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]piperidine-1-carboxylate (intermediate 4) and 4-bromobenzyl bromide were reacted to yield the title compound. 1H NMR (500 MHz, CDCl3) δ 7.49 (d, J 8.2 Hz, 2H), 7.22 (d, J 8.2 Hz, 2H), 4.53 (d, J 12.3 Hz, 1H), 4.44 (d, J 12.3 Hz, 1H), 4.17-3.18 (m, 2H), 3.58-3.51 (m, 1H), 3.43-3.37 (m, 1H), 2.73-2.58 (m, 2H), 1.84 (d, J 13.2 Hz, 1H), 1.70 (d, J 13.3 Hz, 1H), 1.49 (s, 9H), 1.34-1.24 (m, 2H), 1.24-1.17 (m, 1H), 0.94-0.85 (m, 1H), 0.77-0.66 (m, 2H), 0.03-0.02 (m, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b6c2362a2db244e2b8825844b6e6fadb
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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