Sodium borohydride → HCID 58109462, compound

HRID 2037616Notes

Reaction equation

HRID 2037616 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([N:11]2[CH2:16][CH2:15][C:14]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)([CH3:17])[O:13][C:12]2=[O:26])[CH3:10])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[OH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([C@@:14]2([CH3:17])[O:13][C:12](=[O:26])[N:11]([C@H:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH3:10])[CH2:16][CH2:15]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86649950HCID 86649950, compound

Product 1

HCID 58109462HCID 58109462, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.0163 g of 4-(3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-2-oxo-1,3-oxazinan-6-yl)benzaldehyde isomer 2, obtained as described above, and 0.100 g of NaBH4 in MeOH (3 mL) was stirred at room temperature for 24 h. After the solvent was evaporated, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford (S)-6-(4-(hydroxymethyl)phenyl)-3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-1,3-oxazinan-2-one. LC-MS Method 1 tR=1.43 min, m/z 356 (MH+); 1H NMR (400 MHz, CD3OD) δ 7.42-7.25 (m, 4H), 7.14 (d, J=8.8 Hz, 2H), 6.81 (d, J=8.8 Hz, 2H), 5.50 (q, J=7.3 Hz, 1H), 4.53 (s, 2H), 3.69 (s, 3H), 2.70-2.65 (m, 2H), 2.36-2.30 (m, 1H), 1.98-1.87 (m, 1H), 1.50 (s, 3H), 1.19 (d, J=7.3 Hz, 3H).

Workup

  1. customobtained
  2. customAfter the solvent was evaporated
  3. customthe residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%
  4. customover 8 min
  5. wait90% CH3CN/H2O, 0.1% CF3COOH over 2 min

Sources & evidence

ORD record
ord-898bace146c645cba00e6533f28b3930
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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