1-(Bromomethyl)-3-(trifluoromethyl)benzene → (r)-2-[4-(3-Trifluoromethyl-benzyloxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 750040Notes

Reaction equation

HRID 750040 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([C:23]([F:22])([F:32])[F:33])[CH:25]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68996127(r)-2-[4-(3-Trifluoromethyl-benzyloxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 55%

Procedure

Followed the same procedure as that of step 2 in Example 91 with the use of (R)-2-(4-hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (150 mg, 0.5 mmol) and 3-trifluoromethyl-benzyl bromide (145 mg, 0.6 mmol) to afford the title product (120 mg, 55% yield); LCMS; 100% APCI+, Calcd: 451.49. Found m/z: 452.27 (M+1). 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.80-2.09 (m, 4H), 3.26-3.44 (m, 2H), 3.69-3.91 (m, 1H), 4.02-4.18 (m 2H), 5.05 (s, 2H), 6.88 (s, 4H), 7.49 (t, J=7.6 Hz, 1H), 7.57-7.62 (m, 2H), 7.70 (s, 1H).

Sources & evidence

ORD record
ord-9eced2a54f984989b96d18107ef8b56b
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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