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. Author manuscript; available in PMC: 2009 Jan 30.
Published in final edited form as: Synlett. 2006 Nov 13;2007(4):571–582. doi: 10.1002/ejoc.200600767

Table 7.

Synthesis of N-protected pyrrolidines

graphic file with name nihms-87961-t0077.jpg
Entry R P R1 R2 Base Solvent Pd-Source Liganda drb Yield
1 graphic file with name nihms-87961-t0078.jpg Boc H H NaOtBu Toluene Pd(OAc)2 Dppe - 75%c
2 graphic file with name nihms-87961-t0079.jpg Boc H H Cs2CO3 DME Pd(OAc)2 Dpe-phos - 76%
3 graphic file with name nihms-87961-t0080.jpg Ac H H NaOtBu Toluene Pd2(dba)3 Xantphos - 67%
4 graphic file with name nihms-87961-t0081.jpg Cbz H H Cs2CO3 DME Pd(OAc)2 Dpe-phos - 88%
5 graphic file with name nihms-87961-t0082.jpg Boc Ph H NaOtBu Toluene Pd2(dba)3 Dppb >20:1 60%
6 graphic file with name nihms-87961-t0083.jpg Boc Ph H Cs2CO3 Dioxane Pd(OAc)2 Dpe-phos >20:1 75%
7 graphic file with name nihms-87961-t0084.jpg Ac Ph H NaOtBu Toluene Pd2(dba)3 Dppb >20:1 82%
8 graphic file with name nihms-87961-t0085.jpg Boc H Me Cs2CO3 Dioxane Pd(OAc)2 Dpe-phos 15:1 76%
9 graphic file with name nihms-87961-t0086.jpg Ac H Me NaOtBu Toluene Pd2(dba)3 Dpe-phos >20:1 (10:1) 61%
10 graphic file with name nihms-87961-t0087.jpg Cbz H Me Cs2CO3 Dioxane Pd(OAc)2 Dpe-phos 12:1 80%
a

Conditions: 1.0 equiv amine, 1.1-1.2 equiv R-Br, 1.2-2.3 equiv base, 1 mol % Pd2(dba)3 or 2 mol % Pd(OAc)2, 2-4 mol % ligand, toluene or dioxane or dme (0.25 M), 85-105 °C.

b

Diastereomeric ratios are for isolated products. Diastereomeric ratios observed in crude reaction mixtures are given in parentheses if they changed upon isolation.

c

The reaction was conducted at 65 °C.