HCID 89713636, compound → HCID 117737778, compound

HRID 1518971Notes

Reaction equation

HRID 1518971 reaction equation
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[O:9]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]1[C:23]1[S:24][CH:25]=[CH:26][N:27]=1>CO>[OH:9][C@@H:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][C@H:11]1[C:23]1[S:24][CH:25]=[CH:26][N:27]=1

Participants

4

Reactant 2

HCID 89713636HCID 89713636, compoundHCID 131720822Sodium tetraborohydride

Product 1

HCID 117737778HCID 117737778, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium tetraborohydride (535.9 mg, 14.2 mmol) to a solution of tert-butyl 4-oxo-3-(thiazol-2-yl)piperidine-1-carboxylate (4.0 g, 14.2 mmol) in MeOH (175 mL) and stir at ambient temperature for 45 minutes. Quench the reaction mixture with water (100 mL). Concentrate under vacuum to remove MeOH. Extract the aqueous residue with EtOAc (3×100 mL), combine the organic extracts and sequentially wash with water (100 mL) then brine (100 mL). Dry over sodium sulphate; filter; collect the filtrate; and concentrate under vacuum to give the title compound as a mixture of diastereomer pairs (3.9 g). MS (m/z): 285 (M+1).

Workup

  1. customQuench the reaction mixture with water (100 mL)
  2. concentrationConcentrate under vacuum
  3. customto remove MeOH
  4. extractionExtract the aqueous residue with EtOAc (3×100 mL)
  5. washsequentially wash with water (100 mL)
  6. dry with materialDry over sodium sulphate
  7. filtrationfilter
  8. customcollect the filtrate
  9. concentrationand concentrate under vacuum

Sources & evidence

ORD record
ord-9567b0f0b1c748198aed565ef28b5980
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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