Methyl Bromide → HCID 66712473, compound

HRID 631040Notes

Reaction equation

HRID 631040 reaction equation
[CH:1]1([C@@:6]([OH:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]([O:9][C@H:10]2[CH2:15][CH:14]3[N:16]([CH3:17])[C@@H:11]2[CH2:12][CH2:13]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][Br:26]>CC(C)=O>[Br-:26].[CH:1]1([C@@:6]([OH:24])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:7]([O:9][C@H:10]2[CH2:15][CH:14]3[N+:16]([CH3:25])([CH3:17])[C@@H:11]2[CH2:12][CH2:13]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6323Methyl BromideHCID 66712386HCID 66712386, compound

Product 1

HCID 66712473HCID 66712473, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To (1R,2S)-2-((R)-2′-cyclopentyl-2′-hydroxy 2′-phenylacetoxy)-7-methyl-7-azabicyclo[2.2.1]heptane (46 mg, 0.139 mmol) in acetone (2 mL) was added 1 mL of methyl bromide solution (2M in ether). The resulting mixture was left at room temperature for 48 hrs. The crystallized product was filtered off and dried to yield 36 mg of (1R,2S)-2-((R)-2′-cyclopentyl-2′-hydroxy 2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide (2) as a white crystalline solid, M.P. 233-234° C., 1HNMR: 7.6 (dd, 2H); 7.4 (m, 2H); 7.28 (m, 1H); 5.0 (m, 1H); 4.9 (m, 1H); 4.45 (m, 1H); 3.8 (s, 1H); 3.49 (s, 3H); 3.28 (s, 3H); 3.0 (m, 1H); 2.5-2.2 (m, 4H); 1.9-1.3 (m, 10H).

Workup

  1. filtrationThe crystallized product was filtered off
  2. customdried

Sources & evidence

ORD record
ord-a4017aaa890e42f2bc5b3bc413ef3144
Source dataset
uspto-grants-2016_04
Patent number
US09320731B2

Reaction notes

Loading…