Ammonia → HCID 58189243, compound

HRID 1423143Notes

Reaction equation

HRID 1423143 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:34])[C:29]([O:31]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:35].[C-]#N.[Na+]>CO>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:34])[C:29]([NH2:35])=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 86652002HCID 86652002, compound

Product 1

HCID 58189243HCID 58189243, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-ethyl 2-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-2-oxoacetate (245 mg, 0.525 mmol) in a 7 N ammonia solution in MeOH (10 mL) was treated with catalytic amount of sodium cyanide and allowed to stir for 48 h. The reaction mixture was then evaporated, washed with water and air dried to afford a residue then purified by silica gel flash chromatography with 50% then 75% EtOAc/hexanes as eluant to afford the title compound as colorless foam (180 mg, 78%). LC/MS (Method B) 3.31 min, [M+1]+ 438.

Workup

  1. customThe reaction mixture was then evaporated
  2. washwashed with water and air
  3. customdried
  4. customto afford a residue
  5. customthen purified by silica gel flash chromatography with 50%

Sources & evidence

ORD record
ord-24d6a47196164c7b818994fedd61b171
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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