Acetic Acid → HCID 58486214, compound

HRID 2281758Notes

Reaction equation

HRID 2281758 reaction equation
[F:1][C:2]1[CH:9]=[C:8](/[CH:10]=[CH:11]/[B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[F:1][C:2]1[CH:9]=[C:8](/[CH:10]=[CH:11]/[B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)[CH:7]=[CH:6][C:3]=1[CH2:4][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 58486140HCID 58486140, compound

Product 1

HCID 58486214HCID 58486214, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of (E)-2-fluoro-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzaldehyde (0.61 g, 2.2 mmol) and morpholine (0.3 mL) in DCE (20 mL) was added NaBH(OAc)3 (636 mg, 3 mmol), followed by AcOH (0.5 mL). The resulting mixture was stirred for 2 h at rt. The reaction was quenched with sat. NaHCO3 (10 mL), H2O (10 mL), and extracted with EtOAc (2×30 mL). The solvents were removed in vacuo to afford the title compound as a white solid (0.72 g, 94%). 1H NMR (400 MHz, CDCl3) δ 7.20-7.12 (m, 2H), 7.04 (d, J=7.6 Hz, 1H), 6.99 (d, J=10.8 Hz, 1H), 5.98 (d, J=18.4 Hz, 1H), 3.55-3.45 (m, 4H), 3.36 (s, 2H), 2.33-2.23 (m, 4H), 1.14 (s, 12H); MS ESI 348.2 [M+H]+, calcd for [C19H27BFNO3+H]+ 348.2.

Workup

  1. customThe reaction was quenched with sat. NaHCO3 (10 mL), H2O (10 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ab8db34fe7474930a540245d6e6f298e
Source dataset
uspto-grants-2015_09
Patent number
US09139563B2

Reaction notes

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