Sodium borohydride → HCID 118101209, compound

HRID 708876Notes

Reaction equation

HRID 708876 reaction equation
[CH:1]1([C:4](=[O:27])[CH2:5][O:6][C:7]2[C:22]([F:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:8]=2[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([CH:4]([OH:27])[CH2:5][O:6][C:7]2[C:22]([F:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:8]=2[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118101200HCID 118101200, compound

Product 1

HCID 118101209HCID 118101209, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21B (1.47 g, 3.84 mmol) was dissolved in MeOH (15 mL) at 0° C. NaBH4 (0.175 g, 4.61 mmol) was added. The reaction mixture was stirred rt for 1 h. quenched with water, extracted with EtOAc (2×). The extract was dried over sodium sulfate and concentrated. The crude was purified by prep HPLC. To give 21C (830 mg, 2.159 mmol, 56.2% yield). MS (ESI) m/z: 385.4 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 7.95 (dd, J=11.86, 2.20 Hz, 1H) 7.88 (s, 1H) 4.70 (d, J=11.86 Hz, 1H) 4.51 (s, 3H) 4.35 (d, J=13.62 Hz, 1H) 4.20 (t, J=7.91 Hz, 1H) 3.21 (t, J=7.47 Hz, 1H) 2.75 (s, 3H) 1.45 (s, 9H) 0.90 (dd, J=8.13, 4.17 Hz, 1H) 0.49-0.61 (m, 2H) 0.41 (td, J=9.23, 4.83 Hz, 1H) 0.22-0.29 (m, 1H).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude was purified by prep HPLC

Sources & evidence

ORD record
ord-7ca1ab1e7a5c450999e0e22943ffff67
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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