Chlorotrimethylsilane → HCID 24853327, compound

HRID 1015554Notes

Reaction equation

HRID 1015554 reaction equation
N1(C2C=CC([C:12]34[CH2:31][CH:16]5[CH2:17][C:18]([NH:20][CH2:21][C:22]([N:24]6[CH2:28][CH2:27][CH2:26][C@H:25]6[C:29]#[N:30])=[O:23])([CH2:19]3)[CH:14]([CH2:15]5)[CH2:13]4)=CC=2)C=CC=C1.[Si](Cl)(C)(C)C>CO>[CH:16]12[CH2:31][CH:12]3[CH2:13][CH:14]([CH2:15]1)[C:18]([NH:20][CH2:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[C:29]#[N:30])=[O:23])([CH2:19]3)[CH2:17]2

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24853325HCID 24853325, compound

Product 1

HCID 24853327HCID 24853327, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the compound obtained in example 18 (27 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 hydrochloride salt of (2S)-1-[(tricyclo[3.3.1.03,7]non-3-ylamino)acetyl]pyrrolidine-2-carbonitrile as an off-white solid (31 mg). m/z (M+1) 274; 1H NMR (DMSO-d6) 300 MHz δ 9.44 (s (br), 2H), 4.86 (dd, J=4.4, 7.0 Hz, 1H), 4.10-3.88 (m, 2H), 3.78-3.65 (m, 1H), 3.60-3.47 (m, 1H), 2.48-2.41 (m, 1H), 2.34-2.27 (m, 2H), 2.26-2.17 (m, 2H), 2.10-1.99 (m, 2H), 1.99-1.83 (m, 6H), 1.63-1.43 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-0b395e7d823d41deb5c3798b71e9e329
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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