Trifluoroacetic acid → 7-Benzyl-2-oxa-7-azaspiro[4.4]nonan-1-one
Reaction equation
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=[C:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:17][C:18]2([C:19](=[O:20])[O:21][CH2:22][CH2:23]2)[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
A stirred solution of N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (D12, 160 g of 75% purity, assume 0.51 mole) and α-methylene-γ-butyrolactone (D14, 50 g, 0.51 mole) in dichloromethane (11 L) under nitrogen was cooled to 0° C. and then treated with a 1M solution of trifluoroacetic acid in dichloromethane (50ml, 0.05 mole), keeping the temperature below 5° C. The reaction mixture was allowed to warm to room temperature over 2 h, then washed with saturated sodium bicarbonate solution. The aqueous wash was extracted with dichloromethane and the organic solutions then combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to leave a pale yellow oil. This was distilled in vacuo to give the title compound (D15) as a colourless oil (96 g, 81%) b.p. 160°-170° C. at 1 mmHg.
Workup
- customthe temperature below 5° C
- washwashed with saturated sodium bicarbonate solution
- washThe aqueous wash
- extractionwas extracted with dichloromethane
- washwashed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customto leave a pale yellow oil
- distillationThis was distilled in vacuo
Sources & evidence
- ORD record
- ord-3cd9bee9312a45d9acd0edb75624b503
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05278170
Reaction notes
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