Sodium triacetoxyborohydride → HCID 71622960, compound

HRID 1479063Notes

Reaction equation

HRID 1479063 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:31].[O:32]1[CH2:35][C:34](=O)[CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[O:24][CH:25]4[CH2:30][CH2:29][N:28]([CH:34]5[CH2:35][O:32][CH2:33]5)[CH2:27][CH2:26]4)=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:31]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 71610191HCID 71610191, compound

Product 1

HCID 71622960HCID 71622960, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 64 (110 mg; 0.25 mmol; 1 eq.), 3-oxetanone (22 μL; 0.37 mmol; 1.5 eq.) and sodium triacetoxyborohydride (53 mg; 0.25 mmol; 1 eq.) in DCE (6 mL) was stirred at 50° C. for 16 hours. The reaction mixture was diluted with DCM, washed with sat. aq. NaHCO3, dried over sodium sulfate and concentrated in vacuo. Crystallization from EA afforded the title compound (86 mg, 69%) as an off-white solid. 1H NMR (CDCl3) δ 7.34 (td, J=8.1, 6.6 Hz, 1H), 6.80-6.63 (m, 2H), 5.07-4.92 (m, 2H), 4.66 (br s, 2H), 4.61-4.47 (m, 4H), 4.47-4.33 (m, 1H), 3.43-3.28 (m, 1H), 2.92 (s, 1.8H), 2.86 (s, 1.2H), 2.70 (s, 1.2H), 2.63 (s, 1.8H), 2.44-2.28 (m, 2H), 2.23-2.10 (m, 2H), 2.03-1.90 (m, 2H), 1.90-1.73 (m, 2H). HPLC (max plot) 97.1%, Rt 2.90 min. UPLC/MS: (MS+) 500.5 ([M+H]+).

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customCrystallization from EA

Sources & evidence

ORD record
ord-2ef90d7e4f1845d49f58e78ad43e97d2
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

Loading…