Dichloromethane → HCID 89618421, compound

HRID 1476771Notes

Reaction equation

HRID 1476771 reaction equation
C(O)(C(F)(F)F)=O.[Si:8]([O:15][C@H:16]1[CH2:20][N:19](C(OC(C)(C)C)=O)[CH:18]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[CH2:17]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C(Cl)[Cl:37]>>[ClH:37].[Si:8]([O:15][C@H:16]1[CH2:20][NH:19][CH:18]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[CH2:17]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 89618627HCID 89618627, compound

Product 1

HCID 89618421HCID 89618421, compound

Procedure

TFA (0.27 mL, 0.414 g, 3.63 mmol) was added to a solution of (4R)-tert-butyl 4-((tert-butyldimethylsilyl)oxy)-2-(2,5-difluorophenyl)pyrrolidine-1-carboxylate (0.5 g, 1.21 mmol) in DCM (10 mL) at 0° C. and stirring was continued at 28° C. for 2 hr. Reaction mixture was concentrated under reduced pressure to afford (4R)-4-((tert-butyldimethylsilyl)oxy)-2-(2,5-difluorophenyl)pyrrolidine hydrochloride (Int-57). MS (ESI) m/z 200(M-TBDMS+1, free base)

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f3bd386a1b154b69812798e6bfb3c3b7
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

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