Methyl Bromide → HCID 66712473, compound

HRID 402741Notes

Reaction equation

HRID 402741 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-5b975374fa9644a0b25dee7fa93b3d1d
Source dataset
uspto-grants-2014_06
Patent number
US08742131B2

Reaction notes

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