Sodium Carbonate → benzyl (3R,4S)-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate
Reaction equation
[NH:1]1[CH2:5][C@H:4]([CH2:6][OH:7])[C@H:3]([CH2:8][OH:9])[CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>CO.O>[OH:9][CH2:8][C@H:3]1[C@@H:4]([CH2:6][OH:7])[CH2:5][N:1]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:2]1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
(cis)-3,4-Pyrrolidinediyldimethanol (970 mg, 7.4 mmol) was dissolved in a mixture of MeOH (20 mL) and water (7 mL) and cooled to 0° C. Na2CO3 (1.96 g, 19 mmol) was added followed by benzyl chloroformate (1.15 mL, 8.1 mmol) and the resulting solution was stirred for 4 hours, maintaining the temperature at 0° C. The reaction was concentrated under reduced pressure to remove most of the methanol, and the remaining aqueous solution was extracted twice with EtOAc. The combined organics were washed with brine and dried over sodium sulfate before being concentrated in vacuo. RP-HPLC yielded phenylmethyl (cis)-3,4-bis(hydroxymethyl)-1-pyrrolidinecarboxylate (450 mg, 22%, 1.7 mmol). LCMS: (M+H)+: 266.1.
Workup
- temperaturemaintaining the temperature at 0° C
- concentrationThe reaction was concentrated under reduced pressure
- customto remove most of the methanol
- extractionthe remaining aqueous solution was extracted twice with EtOAc
- washThe combined organics were washed with brine
- dry with materialdried over sodium sulfate
- concentrationbefore being concentrated in vacuo
Sources & evidence
- ORD record
- ord-392abbbdac69464fa1d52fc6b45cca57
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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