Sodium borohydride → tert-Butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

HRID 8761Notes

Reaction equation

HRID 8761 reaction equation
[CH:1]([CH:3]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][C:4]1=[O:20])=[CH2:2].[BH4-].[Na+]>CO>[CH:1]([CH:3]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH:4]1[OH:20])=[CH2:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21983959tert-Butyl 1-vinyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 21983968tert-Butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylateYield 104.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 1-vinyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate (0.59 g, 2.11 mmol) from Procedure 17, Step B in methanol (6 mL) was cooled to −70° C. and sodium borohydride (0.022 g, 0.60 mmol) was added. The reaction was allowed to warm to room temperature for 3 h and was then quenched with the addition of 1N hydrochloric acid. The mixture was diluted with water and extracted twice with ether. The combined ether layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to afford the title compound (0.621 g). 1H NMR (400 MHz, CDCl3) indicated a mixture of isomers which was used in the next step.

Workup

  1. customwas then quenched with the addition of 1N hydrochloric acid
  2. additionThe mixture was diluted with water
  3. extractionextracted twice with ether
  4. washThe combined ether layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c841e5b9f76e464caf7e47b43aa62af9
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Reaction notes

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