Trimethylsilyldiazomethane → HCID 67516395, compound

HRID 2173378Notes

Reaction equation

HRID 2173378 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]([C:11]([OH:13])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH3:14][Si](C=[N+]=[N-])(C)C>CO.C(OCC)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 67516507HCID 67516507, compound

Product 1

HCID 67516395HCID 67516395, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-amino-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acid from Step F in methanol (10 mL) was treated dropwise with a solution of trimethylsilyl diazomethane in diethyl ether (2.0 M, 1.96 mL) at 0° C. After complete addition, the reaction warmed to room temperature and stirred 30 min, then was concentrated. The resulting residue was dried under high vacuum to afford methyl 3-amino-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate. 1H NMR (500 MHz, CDCl3), δ 8.26 (s, 1H), 8.19 (s, 1H), 8.05 (br s, 2H), 4.00 (m, 1H), 3.75 (s, 3H), 3.01 (m, 1H), 2.83 (m, 1H), 2.44 (m, 1H), 2.32 (m, 1H); LC/MS (M+1)+=193.0;

Workup

  1. additionAfter complete addition
  2. concentrationwas concentrated
  3. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-fcceaf90661e495487da219b85feb8c7
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…