Triethylamine → N-BOC-3(R)-methylsulfonyloxymethyl-piperidine
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([CH2:26][OH:27])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([CH2:26][O:27][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
2.16 ml of methanesulphonyl chloride followed by 3.86 ml of triethylamine are added to a solution of 5 g of (R)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester in 80 ml of DCM cooled to 0° C. The medium is stirred at 0° C. for 1 h 30 min and 0.7 ml of triethylamine and 0.54 ml of methanesulphonyl chloride are again added. After 30 min at 0° C., the medium is hydrolysed, and the organic phase is washed twice in water and then with a saturated NaCl solution, and then dried over MgSO4. The medium is evaporated, to give 6.8 g of a pale yellow oil.
Workup
- waitAfter 30 min at 0° C.
- washthe organic phase is washed twice in water
- dry with materialwith a saturated NaCl solution, and then dried over MgSO4
- customThe medium is evaporated
Sources & evidence
- ORD record
- ord-f0d21d91905148a0af67c3a60fc88b44
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767681B2
Reaction notes
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