Borate(1-), trifluoro(1-piperidinylmethyl)-, potassium (1:1), (T-4)- → {(S)-6-[(R)-4-Piperidin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422615Notes

Reaction equation

HRID 1422615 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.[N:30]1([CH2:36][B-](F)(F)F)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[K+]>>[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:30]5[CH2:35][CH2:34][CH2:33][CH2:32][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 23706007Borate(1-), trifluoro(1-piperidinylmethyl)-, potassium (1:1), (T-4)-HCID 86700774{(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90313304{(S)-6-[(R)-4-Piperidin-1-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 potassium piperidin-1-ylmethyltrifluoroborate following a procedure analogous to that described for Intermediate 3. LC (method 5): tR=1.15 min; Mass spectrum (ESI+): m/z=490 [M+H]+.

Sources & evidence

ORD record
ord-38c2b61566164b21939b49753ca9ef73
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

Loading…