Acetic Acid → HCID 15233125, compound

HRID 1410358Notes

Reaction equation

HRID 1410358 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C@H:11]1[O:16][C@@H:15]([CH3:17])[CH2:14][NH:13][CH2:12]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:13]2[CH2:12][C@H:11]([CH3:10])[O:16][C@H:15]([CH3:17])[CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 707414-BromobenzaldehydeHCID 6415002,6-Dimethylmorpholine, cis-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15233125HCID 15233125, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-bromobenzaldehyde (3.70 g, 20 mmol) and cis-2,6-dimethylmorpholine (2.52 g, 22 mmol) in DCE (100 mL) was added NaBH(OAc)3 (5.30 g, 25 mmol), followed by AcOH (0.5 mL). After addition, the resulting mixture was stirred 0/N at rt. The reaction as quenched with sat. NaHCO3 (30 mL) and H2O (30 mL), and was extracted with DCM (30 mL×2). Concentration of the solvents afforded the crude title compound as a pale yellow liquid (6.41 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.45 (d, J=7.2 Hz, 2H), 7.21 (d, J=7.2 Hz, 2H), 3.64-3.55 (m, 2H), 3.44 (s, 2H), 2.68 (d, J=11.6 Hz, 2H), 1.75 (t, J=11.0 Hz, 2H), 1.54 (d, J=6.0 Hz, 6H); MS ESI 284.0 [M+H]+, calcd for [C13H18BrNO+H]+ 284.1.

Workup

  1. additionAfter addition
  2. customThe reaction
  3. customas quenched with sat. NaHCO3 (30 mL) and H2O (30 mL)
  4. extractionwas extracted with DCM (30 mL×2)

Sources & evidence

ORD record
ord-c5c974a12b5349ec9e9095dc912e4d05
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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