1,1,1-Trifluorobut-3-en-2-ol → (2S, 4S)-1-N-dodecyl-4-[4-(3-oxo-4,4,4-trifluorobut-1-yl)phenoxy]pyrrolidine-2-carboxylic acid, methyl ester

HRID 1383920Notes

Reaction equation

HRID 1383920 reaction equation
[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=2)[CH2:15][C@H:14]1[C:26]([O:28][CH3:29])=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[F:30][C:31]([F:37])([F:36])[CH:32]([OH:35])[CH:33]=[CH2:34].C(N(CCCC(OCC)=O)CCOC1C=CC(/C=C/C(O)C(F)(F)F)=CC=1)CCCCCCCCCCC>>[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:34][CH2:33][C:32](=[O:35])[C:31]([F:37])([F:36])[F:30])=[CH:21][CH:20]=2)[CH2:15][C@H:14]1[C:26]([O:28][CH3:29])=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 132629561,1,1-Trifluorobut-3-en-2-olHCID 867571214-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl esterHCID 86757129(2S, 4S)-1-N-Dodecyl-4-(4-iodophenoxy)pyrrolidine-2-carboxylic acid, methyl ester

Product 1

HCID 86757816(2S, 4S)-1-N-dodecyl-4-[4-(3-oxo-4,4,4-trifluorobut-1-yl)phenoxy]pyrrolidine-2-carboxylic acid, methyl esterYield 9%

Procedure

(2S, 4S)-1-N-Dodecyl-4-(4-iodophenoxy)pyrrolidine-2-carboxylic acid, methyl ester (800 mg, 1.55 mmol) and 4,4,4-trifluorobut-1-en-3-ol (complex with 1 tetrahydrofuran, 620 mg, 3.1 mmol) were reacted by the general procedure as described in the preparation of 4-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino]butanoic acid, ethyl ester and afforded the title compound (575 mg, 72%) as a colorless oil [[a]D=−28.7° (c 0.8, CHCl3)] and (2S, 4S)-1-N-dodecyl-4-[4-(3-oxo-4,4,4-trifluorobut-1-yl)phenoxy]pyrrolidine-2-carboxylic acid, methyl ester (68 mg, 9%) as a pale yellow oil.

Sources & evidence

ORD record
ord-8b97195004f94079b16c68f770490b8a
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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