Formaldehyde → HCID 66755260, compound

HRID 1643968Notes

Reaction equation

HRID 1643968 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]([CH3:22])[CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 66755114HCID 66755114, compound

Product 1

HCID 66755260HCID 66755260, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-[(1-methyl-piperidin-4-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg, 0.34 mmol) and paraformaldehyde (20 mg, 0.67 mmol) in THF (4 mL) was added MP-(OAc)3BH resin (Argonaut; 2.55 mmol/g; 330 mg, 0.84 mmol) and the reaction mixture was agitated at room temperature for 96 hours. Then, the reaction mixture was filtered and concentrated in vacuo to afford (R)-3-{[methyl-(1-methyl-piperidin-4-yl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (96 mg, 92%) 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-fa090709421d4fdbbf204b21cfcdbe80
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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