Triethylamine → HCID 86640790, compound
Reaction equation
[CH3:1][N:2]1[C@H:8]([CH2:9][OH:10])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[CH3:18][S:19]([O:10][CH2:9][C@@H:8]1[CH2:7][CH2:6][C:3]2([CH2:5][CH2:4]2)[N:2]1[CH3:1])(=[O:21])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (5S)-4-methyl-5-(hydroxymethyl)-4-azaspiro[2.4]heptane (0.2 g, 1.42 mmol) and triethylamine (0.287 g, 2.84 mmol, Shantou Xilong chemical factory) in 5 mL of dichloromethane was stirred at 0° C. for 30 min. To the mixture was added methanesulfonyl chloride (0.325 g, 2.84 mmol, Shanghai Haiqu chemical. Ltd.) via a syringe. The reaction mixture was stirred at 0° C. for 4 hrs and quenched with a mixture of 5 mL of saturated Na2CO3 aqueous solution and 5 mL of water. The resulted mixture was extracted with dichloromethane (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give ((55)-4-methyl-4-azaspiro[2.4]heptane-5-yl)methyl methanesulfonate as yellow oil (150 mg, 48%).
Workup
- stirringThe reaction mixture was stirred at 0° C. for 4 hrs
- customquenched with a mixture of 5 mL of saturated Na2CO3 aqueous solution and 5 mL of water
- extractionThe resulted mixture was extracted with dichloromethane (20 mL×3)
- dry with materialThe combined organic phases were dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-faa94b6df4894bc3a156b2adc71a6b21
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426585B2
Reaction notes
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