Hydrochloric Acid → HCID 55288372, compound
Reaction equation
[OH:1][CH:2]1[CH:6]([CH2:7][S:8][CH3:9])[CH2:5][NH:4][CH2:3]1.CO.Cl>>[OH:1][C@H:2]1[C@H:6]([CH2:7][S:8][CH3:9])[CH2:5][NH:4][CH2:3]1Participants
4
Procedure
N-Protected 3-hydroxy-4-(methylthiomethyl)-pyrrolidine (8.2 g, 33.2 mmol) was dissolved in methanol (40 mL, 33.2 mmol) and to this was added hydrochloric acid (10 mL, 326 mmol) and the resulting solution concentrated in vacuo. This step was repeated, whereupon TLC (10% v/v 7N NH3 in MeOH-dichloromethane) indicated complete deprotection. Column chromatography on silica eluted with 10-20% 7N NH3 in MeOH-dichloromethane afforded the title compound (4.3 g, 29.2 mmol, 88% yield).
Workup
- concentrationthe resulting solution concentrated in vacuo
- washColumn chromatography on silica eluted with 10-20% 7N NH3 in MeOH-dichloromethane
Sources & evidence
- ORD record
- ord-09b2ece7492541ffa9265b2924c6dacd
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183019B2
Reaction notes
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