3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → (S)-5'-(tert-butyldimethylsilyloxy)-4'-(3,6-dihydro-2H-pyran-4-yl)-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehyde

HRID 573725Notes

Reaction equation

HRID 573725 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([CH:25]=[O:26])=[C:11](I)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:28]1[CH2:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH2:30][CH2:29]1>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([CH:25]=[O:26])=[C:11]([C:31]3[CH2:32][CH2:33][O:28][CH2:29][CH:30]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86662517(S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehyde

Product 1

HCID 86662519(S)-5'-(tert-butyldimethylsilyloxy)-4'-(3,6-dihydro-2H-pyran-4-yl)-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehyde

Procedure

Obtained by starting from (S)-5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-83fdcf00214a451db4e35ffe722feaa1
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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