Thionyl Chloride → [2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

HRID 1677206Notes

Reaction equation

HRID 1677206 reaction equation
S(Cl)(Cl)=O.[CH3:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[CH3:17][C:18]1([CH3:34])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=2)[O:19]1>>[CH3:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:29]([C:28]1[CH:27]=[CH:26][C:25]([B:20]2[O:21][C:22]([CH3:24])([CH3:23])[C:18]([CH3:34])([CH3:17])[O:19]2)=[CH:33][CH:32]=1)=[O:30]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 46911921(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidine

Product 1

HCID 57980025[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Procedure

The title intermediate is prepared in a manner substantially analogous General Procedure PP, except thionyl chloride is used instead of oxalyl chloride, using 2-(R)-methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (CAS 180516-87-4). MS (ES+) 399.5 (M+H)+

Sources & evidence

ORD record
ord-3ee822536c4c4e5db4e33f0c434dc15d
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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