Acetic Acid → HCID 59805850, compound

HRID 1429659Notes

Reaction equation

HRID 1429659 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[CH2:11]1[CH2:20][O:19][C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[O:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][N:16]1[CH2:17][CH2:18][C:13]2([O:19][CH2:20][CH2:11][O:12]2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 5880883,4-DifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59805850HCID 59805850, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3,4-difluorobenzaldehyde (4.40 g, 30.9 mmol), 4,4-ethylenedioxy-piperidine (4.40 g, 30.9 mmol), sodium triacetoxyborohydride (6.40 g, 30.2 mmol) and acetic acid (1.8 g, 30.0 mmol) in dichloroethane (200 ml) was stirred at room temperature for 18 h. After this period, the reaction mixture was washed with 1N sodium hydroxide. The organic layer separated, dried (MgSO4) and the solvents evaporated in vacuo to give D3 (7.9 g, 98%). C14H17F2NO2 requires 269; Found 270 (MH+)

Workup

  1. waitAfter this period
  2. washthe reaction mixture was washed with 1N sodium hydroxide
  3. customThe organic layer separated
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-973d092066be432e8254e4b43c05a749
Source dataset
uspto-grants-2015_01
Patent number
US08940743B2

Reaction notes

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