Tetrahydrofuran → 5-((S)-((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-yl)(hydroxy)methyl)-2-(trifluoromethyl)benzonitrile

HRID 573720Notes

Reaction equation

HRID 573720 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]([C:27]3[CH2:28][CH2:29][O:30][CH2:31][CH:32]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:34]1[CH:35]=[CH:36][C:37]([C:42]([F:45])([F:44])[F:43])=[C:38]([CH:41]=1)[C:39]#[N:40].C([Mg]Cl)(C)C.[Cl-].[Li+].C([Mg]Cl)(C)C.[O:58]1CCC[CH2:59]1>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:19][CH:20]([C@H:59]([OH:58])[C:34]3[CH:35]=[CH:36][C:37]([C:42]([F:45])([F:44])[F:43])=[C:38]([CH:41]=3)[C:39]#[N:40])[CH2:21]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:23])[CH3:24])[CH:12]=[C:11]([C:27]3[CH2:28][CH2:29][O:30][CH2:31][CH:32]=3)[C:10]1=2)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 667621505-Iodo-2-(trifluoromethyl)benzonitrileHCID 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'-carbaldehydeHCID 178418918HCID 178418918, compoundHCID 178461733HCID 178461733, compound

Product 1

HCID 667612945-((S)-((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-yl)(hydroxy)methyl)-2-(trifluoromethyl)benzonitrile

Procedure

Obtained by starting from (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 and 5-iodo-2-(trifluoromethyl)benzonitrile. 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-abf96791bb2c4aeb91874dfce2db54e0
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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