Tetrahydrofuran → (S)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3-yl)(4-(pentafluorosulfanyl)phenyl)methanol

HRID 573717Notes

Reaction equation

HRID 573717 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](C=O)=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:29]1[CH:34]=[CH:33][C:32]([S:35]([F:40])([F:39])([F:38])([F:37])[F:36])=[CH:31][CH:30]=1.C([Mg]Cl)(C)C.[Cl-].[Li+].C([Mg]Cl)(C)C.[O:53]1CCC[CH2:54]1>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH:20]([C@@H:54]([C:29]3[CH:34]=[CH:33][C:32]([S:35]([F:40])([F:39])([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[OH:53])[CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:23])[CH3:24])[CH:12]=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 27791994-Iodophenylsulfur PentafluorideHCID 86662517(S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehydeHCID 178418918HCID 178418918, compoundHCID 178461733HCID 178461733, compound

Product 1

HCID 86662516(S)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3-yl)(4-(pentafluorosulfanyl)phenyl)methanol

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 1-iodo-4-pentafluorosulfanyl-benzene. A 1.3 M solution of isopropylmagnesium chloride-lithium chloride-complex in tetrahydrofurane is used instead of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-2de8249dcc7e49b1aa3bc5ae09f298d7
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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