Acetic Acid → HCID 54670022, compound

HRID 2279220Notes

Reaction equation

HRID 2279220 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[CH3:24][N:25]1[CH2:39][CH2:38][N:28]2[C:29]3[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=3[NH:31][CH2:32][CH2:33][CH:27]2[CH2:26]1.C(O)(=O)C>O1CCCC1.Cl>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:31]2[C:30]3[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=3[N:28]3[CH2:38][CH2:39][N:25]([CH3:24])[CH2:26][CH:27]3[CH2:33][CH2:32]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 707414-BromobenzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 67001448HCID 67001448, compound

Product 1

HCID 54670022HCID 54670022, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (200 mg, 0.944 mmol) was added to an ice-cooled solution of 4-bromobenzaldehyde (122 mg, 0.659 mmol) and the product of Example 22F (63 mg, 0.290 mmol) in tetrahydrofuran (5 mL). A few drops of 10% HCl (aq) were added, and the mixture was allowed to warm to room temperature. After 5 hours, acetic acid (2 mL) and additional sodium triacetoxyborohydride (200 mg, 0.944 mmol) were added, and the mixture was stirred an additional 15 hours. The reaction mixture was concentrated under vacuum, and the residue was purified by flash chromatography (SiO2, eluted with CH2Cl2, then CH2Cl2-methanol-15 M NH4OH, 95:5:0.5-90:10:1) to provide the title compound: 1H NMR (300 MHz, CD3OD) δ ppm 1.62 (tt, J=15.3, 5.3, 2.6 Hz, 1H), 1.84-2.00 (m, 1H), 2.33 (t, J=10.9 Hz, 1H), 2.42-2.51 (m, 1H), 2.43 (s, 3H), 2.77 (dt, J=10.7, 2.0 Hz, 1H), 2.85 (ddd, J=11.1, 5.2, 3.6 Hz, 1H), 2.89-3.04 (m, 2H), 3.13 (dt, J=11.9, 2.8 Hz, 1H), 3.30 (s, 1H), 3.45 (td, J=11.3, 2.8 Hz, 1H), 4.22 (d, J=15.1 Hz, 1H), 4.46 (d, J=15.1 Hz, 1H), 6.77-6.96 (m, 4H), 7.27 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H); MS (DCI) m/z 386/388 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by flash chromatography (SiO2
  3. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-86c6c849ecfd48088fc3b54f91267049
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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