Formaldehyde → HCID 66755400, compound

HRID 1631983Notes

Reaction equation

HRID 1631983 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH3:21])[CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 66755285HCID 66755285, compound

Product 1

HCID 66755400HCID 66755400, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-(1-methyl-piperidin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg, 0.35 mmol) and paraformaldehyde (21 mg, 0.71 mmol) in THF (3 mL) MP-(OAc)3BH resin (Argonaut; 2.55 mmol/g; 346 mg, 0.88 mmol) was added and the reaction mixture was agitated at room temperature for 96 hours. Then, the reaction mixture was filtered and concentrated in vacuo to afford (S)-3-[methyl-(1-methyl-piperidin-4-yl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg, 99%) as an orange oil. The residue was used without further purification.

Workup

  1. filtrationThen, the reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a54f3623851495ca950134032187cdb
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

Loading…