Trifluoroacetic acid → (R)-3-(naphth-2-yloxymethyl)pyrrolidine

HRID 1466001Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1.FC(F)(F)C(O)=O>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67351381tert-Butyl (R)-3-(naphth-2-yloxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 26192527(R)-3-(naphth-2-yloxymethyl)pyrrolidineYield 98.9%

Procedure

The procedure is the same as for Example 2 (Stage 2.2) starting from 1.75 g (5.34 mmol) of tert-butyl (R)-3-(naphth-2-yloxymethyl)pyrrolidine-1-carboxylate and 5.00 ml (67.31 mmol) of trifluoroacetic acid. 1.20 g of product are obtained in the form of an oil.

Sources & evidence

ORD record: ord-66c00b8ba5d04935ba21c0720676aa5d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000010B2

Reaction notes

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