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. 2014 Dec 10;80(1):313–366. doi: 10.1021/jo502388r

Table 3. Preparation of 2,5-Diarylpyrrolidine 23 and 1-Nitroso-2,5-diarylpyrrolidine 24.

3.1.1.2.

entry R refa temp (°C) time (h) yieldb (%) refa temp (°C) time (h) yieldb (%)
1 4-MeOC6H4 23a 0c 1 82 24a 0 2 96
2 2-naphthyl 23f 0d 6 81 24f 22 2 92
3 3,5-Me2C6H3 23g 0d 2 86 24g 22 20 96
4 3,5-Ph2C6H3 23h 0d 6 93 24h 22 12 93
5 2-tolyl 23i 0c 2 97f 24i 22 12 95
6 5-Me-2-thienyl 23j 200e 18 ∼64g 24j 0 0.25 57h
a

Reference number for compound.

b

Yield of chromatographed product.

c

Reaction condition A (TMSI) was used.

d

Reaction condition B (TFA) was used.

e

Boc group was removed by heating at 200 °C under argon.

f

Yield of crude product.

g

Cannot completely purify by chromatography.

h

Yield after two steps.