(R)-2-(4-Iodo-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (R)-2-[4-(4-Oxazol-2-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 750090Notes

Reaction equation

HRID 750090 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@@H:21]1[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@@H:21]1[CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([O:12][C:9]2[CH:10]=[CH:11][C:6]([C:2]3[O:1][CH:5]=[CH:4][N:3]=3)=[CH:7][CH:8]=2)=[CH:31][CH:32]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 44819166(R)-2-(4-Iodo-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 1356214594-(Oxazol-2-yl)phenol

Product 1

HCID 69000237(R)-2-[4-(4-Oxazol-2-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 30%

Procedure

The title compound (60 mg, 30%) was prepared from product of step 2 (0.1 g, 0.6 mmol) and (R)-2-(4-Iodo-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.38 g, 0.9 mmol) using the procedure of Example 146, step 3, 1HNMR (400 MHz, CDCl3) δ 7.96 (d, J=8.8 Hz, 2H), 7.67 (s, 1H), 7.20 (s, 1H), 6.92 (m, 6H), 4.13 (m, 2H), 3.86 (m, 1H), 3.41 (m, 2H), 2.07-1.78 (m, 4H), 1.48 (s, 9H)

Sources & evidence

ORD record
ord-bc6fae79f65e47a18ade1ff4c7fd6bbc
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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