Formaldehyde → HCID 86625771, compound

HRID 2378005Notes

Reaction equation

HRID 2378005 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH:12]1[C:17](=[O:22])[N:18]([O:20][CH3:21])[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:25])[CH2:13][CH:12]1[C:17](=[O:22])[N:18]([O:20][CH3:21])[CH3:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86625770HCID 86625770, compound

Product 1

HCID 86625771HCID 86625771, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To (RS)-2-(methoxy-methyl-carbamoyl)-piperazine-1-carboxylic acid benzyl ester, D52 (3 g, 10 mmol) in 1,2-dichloroethane (50 ml) was added formaldehyde (0.85 ml of 37% w/w solution in water, 11 mmol) and the mixture stirred at ambient temperature for 0.75 h. Sodium triacetoxyborohydride (2.55 g, 12 mmol) was added portionwise over 0.25 h, and the resulting mixture stirred at ambient temperature for 18 h. The reaction was partitioned between dichloromethane (300 ml) and 1M sodium hydroxide (100 ml). The aqueous was re-extracted with dichloromethane (250 ml) and the combined extracts dried (Na2SO4) and the solvent removed in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate-hexane mixtures to afford the title product (3 g, 96%) as a gum.

Workup

  1. stirringthe resulting mixture stirred at ambient temperature for 18 h
  2. customThe reaction was partitioned between dichloromethane (300 ml) and 1M sodium hydroxide (100 ml)
  3. extractionThe aqueous was re-extracted with dichloromethane (250 ml)
  4. dry with materialthe combined extracts dried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-84c3ce7df7d84e74a15b2cc59a1aaff9
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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