Ammonium Chloride → 1-[2-(2-Hydroxymethyl-4-bromophenoxy)ethyl]pyrrolidine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:12]([CH:15]=1)[CH:13]=[O:14].[Cl-].[NH4+]>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:12]([CH2:13][OH:14])[CH:15]=1Participants
Procedure
3.4 mL (3.40 mmol) of a lithium aluminum hydride solution (1M in THF) was added under argon at 0° C. to a solution of 1.00 g (3.35 mmol) of 5-bromo-2-(2-pyrrolidin-1-ylethoxy)benzaldehyde (Example 24.1a) in 20 mL of THF and the mixture was stirred for 2 hours at RT. A further 6.8 mL of lithium aluminum hydride solution (1M in THF) was added and the mixture was stirred for 2 hours at RT. The reaction mixture was slowly combined with sat. aqueous ammonium chloride solution and the aqueous phase was exhaustively extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. As some starting material could still be detected, the reaction was repeated with 1.7 mL of lithium aluminum hydride solution (1M in THF) and the working up was repeated. Yield: 0.82 g (81% of theoretical); C13H18BrNO2 (M=300.192); calc.: molpeak (M+H)+: 300/302 (Br); found: molpeak (M+H)+: 300/302 (Br); HPLC-MS: 4.62 minutes (method A).
Workup
- stirringthe mixture was stirred for 2 hours at RT
- extractionthe aqueous phase was exhaustively extracted with EtOAc
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- customevaporated down in vacuo
- custom4.62 minutes (method A)
Sources & evidence
- ORD record
- ord-92704a9ac97644fcae8dba60b1d78275
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592358B2
Reaction notes
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