Formaldehyde → HCID 66980534, compound

HRID 1038801

Reaction equation

HRID 1038801 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:29]=[O:30]>C1COCC1>[C:1]([C:3]1([CH2:29][OH:30])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 66980534HCID 66980534, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of benzyl 4-cyanopiperidine-1-carboxylate (1.0 g, 4.0 mmol, Oakwood) in THF (50 mL) at about −78° C. was added LiHMDS (1.0 M solution in THF, 6.14 mL, 6.14 mmol) dropwise via syringe. The mixture was stirred for about 1 h. Paraformaldehyde (0.25 g, 8.2 mmol) was added in one portion and the mixture was stirred overnight at rt. The mixture was concentrated in vacuo and the residue was purified by preparative TLC (1:1 EtOAc/pet ether) to give benzyl 4-cyano-4-(hydroxymethyl)piperidine-1-carboxylate (0.45 g, 35%): LC/MS (Table 2, Method k) Rt=0.60 min; MS m/z: 274 (M+H)+.

Workup

  1. stirringthe mixture was stirred overnight at rt
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by preparative TLC (1:1 EtOAc/pet ether)

Sources & evidence

ORD record
ord-5c54e5ae32254843bbadc584dacfc6c3
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Linked notes

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