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. 2023 Jan 10;25(2):400–404. doi: 10.1021/acs.orglett.2c04095

Table 1. Optimization Studies.

graphic file with name ol2c04095_0006.jpg

entry acylating agent (equiv) solvent, time yield of 2 (%)a yield of 3 (%)a
1b TrocCl (1.5) CHCl3, 18 h 60 (52) 10 (9)
2b TCBocCl (1.5) CHCl3, 18 h 85 0
3 Boc2O (1.5) CHCl3, 7 days 81 0
4 Boc2O (5.0) CHCl3, 6 days 88 0
5c Boc2O (1.5) CHCl3, 18 h 0 96
6 Boc2O (1.5) MeCN, 48 h 44 0
7 Boc2O (5.0) MeCN, 24 h 85 (68) 0
a

Yield determined by 19F NMR. Isolated yields in parentheses.

b

Reaction performed at room temperature with DIPEA (1.5 equiv).

c

With DMAP (0.3 equiv).