Acetic Acid → HCID 68511081, compound

HRID 1714035Notes

Reaction equation

HRID 1714035 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[O:18][CH2:17][C:16](=O)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([NH:36][CH2:35][CH2:34][N:33]([CH3:37])[CH3:32])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 68505502HCID 68505502, compound

Product 1

HCID 68511081HCID 68511081, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of foregoing crude ketone (from Step 4) in DCE (0.06 M) was added N,N-dimethylethane-1,2-diamine (1.0 eq) and HOAc (1.5 eq.), followed by solid sodium triacetoxyborohydride (1.5 eq). NaOH (20 eq., 1 N) was added after 16 h, and after stirring for 5 min the mixture was taken into EtOAc and washed with water and brine. Drying over Na2SO4 and concentration i. vac. gave the crude product, which was used without further purification; MS (ES+) m/z 494 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialDrying over Na2SO4 and concentration i

Sources & evidence

ORD record
ord-bb2197fb7f6240e1b7006577a0c716d2
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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