Triethylamine → (R)-5-methanesulphonyloxy-5-(3-pyridyl)pentyl thioacetate
Reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]([OH:16])[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(=[S:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(=[S:3])[CH3:2]Participants
Procedure
A solution of (R)-5-hydroxy-5-(3-pyridyl)pentyl thioacetate (2.8 g) in dry dichloro- methane (15 ml) under a nitrogen atmosphere is cooled to -15° C. and treated with triethylamine (1.4 g) using a syringe. It is then treated with methanesulphonyl chloride (1.5 g) by syringe during 5 minutes. The temperature rises spontaneously to -8° C. during this addition. When the addition is complete the reaction mixture is allowed to warm to room temperature. After 2 hours it is washed with water (4×15 ml) until its pH is 7. The organic phase is then dried with magnesium sulphate, filtered and evaporated under reduced pressure, to give (R)-5-methanesulphonyloxy-5-(3-pyridyl)pentyl thioacetate (3.66 g), in the form of a yellow oil. This material is used in the next step without further purification.
Workup
- additionThe temperature rises spontaneously to -8° C. during this addition
- additionWhen the addition
- washAfter 2 hours it is washed with water (4×15 ml) until its pH is 7
- dry with materialThe organic phase is then dried with magnesium sulphate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a94413a8d76b48e886879a7cd1e158e1
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688954
Reaction notes
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