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

HRID 1036706
ノート
印刷プレビュー

反応式

HRID 1036706 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24385
Nickel Dichloride
触媒
HCID 702Ethanol溶媒
HCID 887Methanol溶媒

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-eebdefd8b11d43c7b2b2034742ba6fa3
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546416B2

反応ノート

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