Potassium (4-tert-butoxycarbonylpiperazin-1-yl)methyltrifluoroborate → {(S)-6-[(R)-4-(4-tert-Butoxycarbonyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422612Notes

Reaction equation

HRID 1422612 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.[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][N:40]([CH2:43][B-](F)(F)F)[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31].[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]([CH2:43][N:40]5[CH2:41][CH2:42][N:37]([C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])[CH2:38][CH2:39]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 45588144Potassium (4-tert-butoxycarbonylpiperazin-1-yl)methyltrifluoroborateHCID 86700774{(S)-6-[(R)-4-bromo-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90314350{(S)-6-[(R)-4-(4-tert-Butoxycarbonyl-piperazin-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 (4-tert-butoxycarbonyl-piperazin-1-yl)methyltrifluoroborate following a procedure analogous to that described for Intermediate 3. LC (method 1): tR=1.26 min; Mass spectrum (ESI+): m/z=591 [M+H]+.

Sources & evidence

ORD record
ord-90285c3af6694306bdec12bad1138cb4
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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