Sodium Iodide → (2S,4S)-4-Fluoro-1-({[2,4,6-trimethyltetrahydro-2H-pyran-4-yl]amino}acetyl)-2-pyrrolidinecarbonitrile

HRID 456740Notes

Reaction equation

HRID 456740 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]([NH2:9])([CH3:8])[CH2:5][CH:4]([CH3:10])[O:3]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][C:19]([N:21]1[CH2:25][C@@H:24]([F:26])[CH2:23][C@H:22]1[C:27]#[N:28])=[O:20].[Na+].[I-]>O1CCCC1>[F:26][C@@H:24]1[CH2:25][N:21]([C:19](=[O:20])[CH2:18][NH:9][C:6]2([CH3:8])[CH2:5][CH:4]([CH3:10])[O:3][CH:2]([CH3:1])[CH2:7]2)[C@H:22]([C:27]#[N:28])[CH2:23]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 184373242,4,6-Trimethyloxan-4-amineHCID 57518632(2S,4S)-1-(2-Chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 69331893(2S,4S)-4-Fluoro-1-({[2,4,6-trimethyltetrahydro-2H-pyran-4-yl]amino}acetyl)-2-pyrrolidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2,4,6-Trimethyltetrahydro-2H-pyran-4-yl)amine obtained in Example 9-4 (900 mg) and K2CO3 (1.2 g) in tetrahydrofuran (10 mL) cooled on an ice bath, were added (2S,4S)-1-(chloroacetyl)-4-fluoro-2-pyrrolidinecarbonitrile obtained in Example 7-11 (700 mg) and a catalytic amount of NaI. The reaction mixture was warmed to room temperature and stirred for 65 hrs.

Workup

  1. temperaturecooled on an ice bath

Sources & evidence

ORD record
ord-cd7dc86ab81347b28ca39aa9b0c40a76
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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