Borohydride → HCID 57659379, compound

HRID 1009820Notes

Reaction equation

HRID 1009820 reaction equation
[BH4-].[Na+].[BH4-].CO[C:6](=[O:31])[CH2:7][CH:8]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9]1>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[O:31]=[C:6]1[O:30][CH:29]2[C:28]3[C:23]([C:10]4([CH2:9][CH:8]2[CH2:7]1)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:11]4)=[CH:24][CH:25]=[CH:26][CH:27]=3

Participants

6

Reactant 3

HCID 28123Borohydride2×HCID 4311764Sodium borohydrideHCID 57659356HCID 57659356, compound

Product 1

HCID 57659379HCID 57659379, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Zn(BH4)2 was prepared following a known procedure (Beatrix Merla, Hans-Joachim Grumbach, Nikolaus Risch, Synthesis, 1998 1609-1614). At 0° C., zinc chloride (anhydrous, 5 g, 36.6 mmol) was added to a solution of sodium borohydride (2.72 g, 72 mmol) in diethyl ether (100 ml). The reaction mixture was stirred at 0° C. for 2 h. After filtration under N2, the borohydride solution (9 ml) was added to a suspension of the tert-butyl 3-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (589 mg, 1.52 mmol). After 1 h, additional borohydride solution (9 ml) was added and the mixture stirred for 15 h. The mixture was quenched with 1N HCl, neutralized with saturated sodium bicarbonate, extracted with EtOAc. The extract was concentrated and the residue purified by flash chromatography to give the title compound (140 mg).

Workup

  1. customa known procedure (Beatrix Merla, Hans-Joachim Grumbach, Nikolaus Risch, Synthesis, 1998 1609-1614)
  2. filtrationAfter filtration under N2
  3. waitAfter 1 h
  4. stirringthe mixture stirred for 15 h
  5. customThe mixture was quenched with 1N HCl
  6. extractionextracted with EtOAc
  7. concentrationThe extract was concentrated
  8. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-b048bb42278a4f5395b32a7cfad3ab7d
Source dataset
uspto-grants-2011_07
Patent number
US07973162B2

Reaction notes

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