Methyl Bromide → HCID 66712473, compound

HRID 1969500Notes

Reaction equation

HRID 1969500 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-13dd72158250479d8028466c6454cd12
Source dataset
uspto-grants-2013_04
Patent number
US08426611B2

Reaction notes

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