Triethylamine → (S)-tert-Butyl 2-((benzo[b]thiophen-5-yloxy)methyl)pyrrolidine-1-carboxylate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:34][CH2:35][C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].[S:48]1[CH:52]=[CH:51][C:50]2[CH:53]=[C:54](O)[CH:55]=[CH:56][C:49]1=2.C(N(CC)CC)C>ClCCl>[S:48]1[CH:52]=[CH:51][C:50]2[CH:53]=[C:54]([O:34][CH2:35][C@@H:36]3[CH2:40][CH2:39][CH2:38][N:37]3[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH:55]=[CH:56][C:49]1=2Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Polystyrene supported triphenylphosphine (2.9 mmol/g, 1.70 g, 4.95 mmol) was treated with diisopropylazodicarboxylate (0.779 mL, 3.96 mmol) at 0° C. in anhydrous dichloromethane. A mixture of (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.5 g, 3.3 mmol), benzo[b]thiophen-5-ol (0.5 g, 3.3 mmol) and triethylamine (0.689 mL, 4.95 mmol) in dichloromethane (5 mL) was then added to the reaction. The mixture was then allowed to warm up to room temperature and stirred overnight. The reaction was then filtered off and the filtrate purified by column chromatography on silica gel using a gradient of 15 to 50% ethyl acetate in hexanes to obtain a clear oil that solidied into an off-white solid on standing. Yield=0.48 g. MS (M+H)+ 334.
Workup
- additionwas then added to the reaction
- filtrationThe reaction was then filtered off
- customthe filtrate purified by column chromatography on silica gel using a gradient of 15 to 50% ethyl acetate in hexanes
- customto obtain a clear oil that
Sources & evidence
- ORD record
- ord-c08d23a6c80a46cd94b118f6d4b30459
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786132B2
Reaction notes
Loading…