Formaldehyde → HCID 71284724, compound

HRID 1481799Notes

Reaction equation

HRID 1481799 reaction equation
[CH2:1]([NH:8][C@@H:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([Br:21])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][C@@H:10]1[CH2:22][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([N:8]([CH3:26])[C@@H:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([Br:21])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][C@@H:10]1[CH2:22][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71284558HCID 71284558, compound

Product 1

HCID 71284724HCID 71284724, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The product of Step 1 (710 mg, 2 mmol) was suspended in 1,2-dichloroethane with formaldehyde (0.4 mL of 37% aqueous solution, 5 mmol). Sodium triacetoxyborohydride (848 mg, 4 mmol) was added to the mixture. The mixture stirred vigorously at room temperature for 30 min. The mixture was washed with aqueous saturated NaHCO3 and run through a plug of silica gel, eluting with EtOAc, to give the product (690 mg, 90%).

Workup

  1. washThe mixture was washed with aqueous saturated NaHCO3
  2. washeluting with EtOAc

Sources & evidence

ORD record
ord-2b7b9122097b430e8b82a3876fabca0f
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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