Formaldehyde → HCID 91012362, compound

HRID 459935Notes

Reaction equation

HRID 459935 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8]([N:10]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].C=O.[C:32](OC(OC(=O)C)(OC(=O)C)C(O[BH3-])=O)(=O)C.[Na+]>ClCCCl>[Cl:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8]([N:10]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])[CH2:15][CH2:14][N:13]([CH3:32])[CH2:12][CH2:11]1)=[O:9]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 131726308HCID 131726308, compoundHCID 131726309HCID 131726309, compound

Product 1

HCID 91012362HCID 91012362, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of example 6 (51 mg), aqueous formaldehyde (33 μL) and sodium triacetoxyacetoxyborohydride (50 mg) in anhydrous 1,2-dichloroethane (2 mL) was stirred at r.t. overnight. The mixture was washed with water (2 mL) and brine (2 mL) and concentrated in vacuo. The residue was purified by flash chromatography (AcOEt 100%) to give 7-(R)-(4-fluoro-2-methyl-phenyl)-4-methyl-[1,4]-diazepane-1-carboxylic acid, (3,5-dichloro-benzyl)-methylamide (10 mg).

Workup

  1. washThe mixture was washed with water (2 mL) and brine (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (AcOEt 100%)

Sources & evidence

ORD record
ord-535b6811ec9d405081dc0a7421f501bf
Source dataset
uspto-grants-2007_03
Patent number
US07196077B2

Reaction notes

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