Phenol → (S)-Tert-Butyl 3-phenoxypyrrolidine-1-carboxylate
Reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[O:13]([C@H:10]1[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
5
Procedure
Di-isopropylazodicarboxylate (5.7 mL, 29.38 mmol) was added to an ice-cooled solution of (R)-(−)-N-boc-3-pyrrolidinol (5 g, 26.71 mmol), phenol (2.51 g, 26.71 mmol) and triphenyl phosphine (7.71 g, 29.38 mmol) in tetrahydrofuran (70 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and the residue was twice triturated with diethyl ether and filtered. The filtrate was washed with 1N sodium hydroxide solution (20 mL), dried over sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with pentane:ethyl acetate, 90:10 to 83:17, afforded the title compound as a colourless oil in 75% yield, 5.27 g.
Workup
- concentrationThe reaction mixture was then concentrated in vacuo
- customthe residue was twice triturated with diethyl ether
- filtrationfiltered
- washThe filtrate was washed with 1N sodium hydroxide solution (20 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customPurification of the residue by column chromatography on silica gel
- washeluting with pentane
Sources & evidence
- ORD record
- ord-20b0af26d29e4f68b167af9766033906
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268881B2
Reaction notes
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