Methanol → (2S)-1-{N-[2-(2-oxopyrrolidin-1-yl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile

HRID 1015565Notes

Reaction equation

HRID 1015565 reaction equation
O=C1NCCN1C1C=CC([C:13]23[CH2:32][CH:17]4[CH2:18][C:19]([NH:21][CH2:22][C:23]([N:25]5[CH2:29][CH2:28][CH2:27][C@H:26]5[C:30]#[N:31])=[O:24])([CH2:20]2)[CH:15]([CH2:16]4)[CH2:14]3)=CC=1.[Si](Cl)(C)(C)C.[CH3:38][OH:39]>>[O:39]=[C:38]1[CH2:17][CH2:18][CH2:19][N:21]1[C:13]12[CH2:32][CH:17]3[CH2:18][C:19]([NH:21][CH2:22][C:23]([N:25]4[CH2:29][CH2:28][CH2:27][C@H:26]4[C:30]#[N:31])=[O:24])([CH2:20]1)[CH:15]([CH2:16]3)[CH2:14]2

Participants

4

Reactant 3

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 24853326HCID 24853326, compound

Product 1

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

Procedure

To a stirred solution of the compound obtained from example 19 (36 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 ether to obtain the hydrochloride salt of (2S)-1-{N-[2-(2-oxopyrrolidin-1-yl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as off-white solid (38 mg).

Workup

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

Sources & evidence

ORD record
ord-e3c6893f43c8401e867694940d3cad41
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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