Chlorotrimethylsilane → (2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile

HRID 1015570Notes

Reaction equation

HRID 1015570 reaction equation
O=C1CCCN1[C:7]12[CH2:26][CH:11]3[CH2:12][C:13]([NH:15][CH2:16][C:17]([N:19]4[CH2:23][CH2:22][CH2:21][C@H:20]4[C:24]#[N:25])=[O:18])([CH2:14]1)[CH:9]([CH2:10]3)[CH2:8]2.[Si](Cl)(C)(C)C>CO>[C:7]1([C:7]23[CH2:26][CH:11]4[CH2:12][C:13]([NH:15][CH2:16][C:17]([N:19]5[CH2:23][CH2:22][CH2:21][C@H:20]5[C:24]#[N:25])=[O:18])([CH2:14]2)[CH:9]([CH2:10]4)[CH2:8]3)[CH:26]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24853439(2S)-1-{N-[2-(2-oxopyrrolidin-1-yl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile

Product 1

HCID 24853441(2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrileYield 217.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the compound obtained from example 26 (35 mg, 0.1 mmol) in methanol (2 mL) cooled to 0° C. was added TMS-Cl (25 μL, 0.2 mmol). After 30 minutes, the volatiles were removed under reduced pressure and the residue was triturated several times with diethyl ether to obtain the hydrochloride salt of (2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile as an off-white solid (38 mg).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe residue was triturated several times with diethyl ether

Sources & evidence

ORD record
ord-370219fe08c84fd2a08708055629c403
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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