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

HRID 1036706
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HRID 1036706 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24385
Nickel Dichloride
촉매
HCID 702Ethanol용매
HCID 887Methanol용매

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-eebdefd8b11d43c7b2b2034742ba6fa3
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546416B2

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