Sodium borohydride → 5-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-methylthio-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

HRID 1713158Notes

Reaction equation

HRID 1713158 reaction equation
[I-].[CH:2]1([N:6]2[CH2:11][CH2:10][N:9]([C:12](=[O:25])[CH2:13][N+:14]3[CH:19]=[CH:18][C:17]4[N:20]=[C:21]([S:23][CH3:24])[O:22][C:16]=4[CH:15]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[CH:2]1([N:6]2[CH2:7][CH2:8][N:9]([C:12](=[O:25])[CH2:13][N:14]3[CH2:19][CH2:18][C:17]4[N:20]=[C:21]([S:23][CH3:24])[O:22][C:16]=4[CH2:15]3)[CH2:10][CH2:11]2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86615414HCID 86615414, compound

Product 1

HCID 594635975-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-methylthio-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solid from Step 1 is dissolved in MeOH and NaBH4 (210 mg, 5.56 mmol) is added to the solution. The solution is heated at reflux for 4 hr, and then cooled to rt. The solvent is removed in vacuo and the residue is partitioned between water (6 mL) and EtOAc (6 mL). The layers are separated and aqueous layer is extracted with EtOAc (6 ml). The combined extracts are washed with brine (5 ml), dried and evaporated. The residue is purified by PTLC to give the title compound as a light yellow oil. MS (M+1): 351.0; 1H NMR (δ, CDCl3): 3.55-3.65 (m, 6H), 3.40 (s, 2H), 2.87 (t, 2H), 2.65-2.76 (m, 1H), 2.54-2.62 (m, 5H), 2.28 (t, 4H), 1.64-2.06 (m, 6H)

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 4 hr
  3. customThe solvent is removed in vacuo
  4. customthe residue is partitioned between water (6 mL) and EtOAc (6 mL)
  5. customThe layers are separated
  6. extractionaqueous layer is extracted with EtOAc (6 ml)
  7. washThe combined extracts are washed with brine (5 ml)
  8. customdried
  9. customevaporated
  10. customThe residue is purified by PTLC

Sources & evidence

ORD record
ord-6f9c574492044ba2ae7fc8bfe605d28a
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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