Formaldehyde → HCID 67264976, compound

HRID 1685189Notes

Reaction equation

HRID 1685189 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([C@@H:30]3[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C1COCC1>CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]([C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32]([CH3:38])[CH2:31]3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:28])([F:27])[F:29])[CH:20]=3)[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 67265161HCID 67265161, compound

Product 1

HCID 67264976HCID 67264976, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-[(R)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1-piperidin-3-yl-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.49 mmol; 741 mg); formaldehyde (5 equiv; 7.46 mmol; 560 μL); sodium triacetoxyborohydride (2 equiv; 2.98 mmol; 632 mg) and THF (25 mL) and stir at 20° C. for 20 min. Dilute with EA, wash the organic phase 2× with saturated sodium bicarbonate, brine, dry over MgSO4, filter and evaporate to provide the title compound (790.3 mg; 1.55 mmol; 104%). MS (ES+): m/z=511 (M+H).

Workup

  1. washwash the organic phase 2× with saturated sodium bicarbonate, brine
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. customevaporate

Sources & evidence

ORD record
ord-a42ef0538cce4551b24e50fcbdfe4ffc
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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