{(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → {(S)-6-[(R)-4-(3-Aza-bicyclo[3.1.0]hex-3-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422620Notes

Reaction equation

HRID 1422620 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19](Br)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[CH:30]12[CH2:35][CH:34]1[CH2:33][NH+:32]([CH2:36][B-](F)(F)F)[CH2:31]2>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:36][N:32]5[CH2:33][CH:34]6[CH:30]([CH2:35]6)[CH2:31]5)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

3

Reactant 2

HCID 86700774{(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 90314135HCID 90314135, compound

Product 1

HCID 90313876{(S)-6-[(R)-4-(3-Aza-bicyclo[3.1.0]hex-3-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Procedure

The title compound is prepared from {(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and (3-azonia-bicyclo[3.1.0]hex-3-yl)methyltrifluoroborate following a procedure analogous to that described for Intermediate 3. LC (method 1): tR=0.96 min; Mass spectrum (ESI+): m/z=488 [M+H]+.

Sources & evidence

ORD record
ord-b7a0d4c6be5c43cb8907c110ccfde1a9
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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