Sodium borohydride → HCID 21978391, compound

HRID 10218Notes

Reaction equation

HRID 10218 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH2:12]1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][N:11]1[CH2:12][CH:13]([CH2:15][CH:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[OH:17])[CH2:14]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride4×HCID 21978376HCID 21978376, compound

Product 1

HCID 21978391HCID 21978391, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-{1-[2-(2,4-difluorophenyl)ethyl]azetidin-3-yl}-1-phenylethanone (Example 20, 41 mg, 0.117 mmol) in methanol (1 mL) under nitrogen was added sodium borohydride (8.8 mg, 0.23 mmol). The reaction was stirred at room temperature overnight. More sodium borohydride (5 mg, 0.13 mmol) was added and the reaction stirred for 30 minutes. More sodium borohydride (8.8 mg, 0.23 mmol) was added and the reaction stirred for 15 minutes. More sodium borohydride (5 mg, 0.13 mmol) was added and the reaction stirred overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica, eluting with 10% methanol/dichloromethane, to give the title compound. 1H NMR (360 MHz, CDCl3) δ 7.35–7.29 (5H, m), 7.22–7.16 (1H, m), 6.81–6.73 (2H, m), 4.71 (1H, dd, J=5.3, 7.6 Hz), 3.63 (1H, s), 3.53 (1H, s), 3.11 (1H, s), 2.98 (1H, s), 2.77 (5H, s), 2.07–1.92 (2H, m); m/z (ES+) 318 (M+H)+.

Workup

  1. stirringthe reaction stirred for 30 minutes
  2. stirringthe reaction stirred for 15 minutes
  3. stirringthe reaction stirred overnight
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by flash column chromatography on silica
  6. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-95053423c5504bcd8ef793265d775e54
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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