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Ammonia → Tert-butyl 1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

HRID 1036706
Notes
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Reaction equation

HRID 1036706 reaction equation
[BH4-].[Na+].[N+:3]([CH2:6][CH:7]([C:14]1([C:28]([O:30]C)=O)[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-])=O.N.CCOC(C)=O>CCO.CO.Cl[Ni]Cl>[O:30]=[C:28]1[C:14]2([CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:16][CH2:15]2)[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][NH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 710601881-tert-Butyl 4-methyl 4-(2-nitro-1-phenylethyl)azepane-1,4-dicarboxylate

Product 1

HCID 71060671Tert-butyl 1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

Reagents, catalysts & solvents 3

HCID 24385
Nickel Dichloride
Catalyst
HCID 702EthanolSolvent
HCID 887MethanolSolvent

Procedure

NaBH4 (570 mg, 15.03 mmol) in EtOH (15 ml) under nitrogen was stirred for 20 minutes and added portionwise (4 aliquots) to a cooled (ice-bath) mixture comprising 1-tert-butyl 4-methyl 4-(2-nitro-1-phenylethyl)azepane-1,4-dicarboxylate (step 2) (1.079 g, 2.504 mmol) and NiCl2 (595 mg, 2.504 mmol) in MeOH (25 ml). After stirring at RT for 1 hour, sat. ammonia solution was added (50 ml) followed by EtOAc (60 ml). The mixture was reduced in vacuo and the resulting slurry was partitioned between sat. ammonia solution and EtOAc. The organic portion was separated and the aqueous was further extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with 1-10% MeOH in TBME afforded the title compound;

Workup

  1. additionadded portionwise (4 aliquots) to
  2. customthe resulting slurry was partitioned between sat. ammonia solution and EtOAc
  3. customThe organic portion was separated
  4. extractionthe aqueous was further extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica eluting with 1-10% MeOH in TBME

Sources & evidence

ORD record
ord-eebdefd8b11d43c7b2b2034742ba6fa3
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546416B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes