Sodium borohydride → HCID 57911483, compound

HRID 1666152Notes

Reaction equation

HRID 1666152 reaction equation
[BH4-].[Na+].[C:3]([NH:7][C:8]1[N:13]=[C:12]2[C:14](=[O:27])[CH2:15][CH2:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])[CH2:18][C:11]2=[CH:10][CH:9]=1)([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([NH:7][C:8]1[N:13]=[C:12]2[C@H:14]([OH:27])[CH2:15][CH2:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])[CH2:18][C:11]2=[CH:10][CH:9]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57911477HCID 57911477, compound

Product 1

HCID 57911483HCID 57911483, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

SODIUM BOROHYDRIDE (0.072 g, 1.893 mmol) was added to the MeOH (10 mL) solution of (R)-2-(tert-butylamino)-6-(2,3-difluorophenyl)-7,8-dihydro-5H-cyclohepta[b]pyridin-9(6H)-one (0.2173 g, 0.631 mmol) at rt. The reaction was stirred at room temperature for 1 hour. LCMS showed the reaction was finished. The solvent was removed via vacuum. The crude was separated via flash column eluted with ethyl acetate in hexane from 0 to 35% to 65% to give two compounds. This is the less polar compound (134.9 mg, 61%). HPLC tR=2.43 min; MS(ESI)[M+H+]=347.33; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.18 (d, J=8.06 Hz, 1H) 6.99-7.11 (m, 3H) 6.28 (d, J=8.06 Hz, 1H) 4.76 (dd, J=11.33, 2.01 Hz, 1H) 4.53 (br.s., 1H) 3.03 (d, J=13.85 Hz, 1H) 2.89 (d, J=4.28 Hz, 1H) 2.64 (d, J=14.10 Hz, 1H) 2.28 (dd, J=12.59, 2.01 Hz, 1H) 2.13 (dd, J=9.82, 3.78 Hz, 2H) 1.58-1.71 (m, 1H) 1.42-1.55 (m, 9H).

Workup

  1. customThe solvent was removed via vacuum
  2. customThe crude was separated via flash column
  3. washeluted with ethyl acetate in hexane from 0 to 35% to 65%
  4. customto give two compounds

Sources & evidence

ORD record
ord-d9df51065c7c4bf2a09999a32ed5f74e
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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