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Sodium triacetoxyborohydride → {2-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 553483
ノート
印刷プレビュー

反応式

HRID 553483 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[C:20]([O:24][C:25](=[O:31])[N:26]([CH3:30])[CH2:27][CH:28]=O)([CH3:23])([CH3:22])[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:20]([O:24][C:25](=[O:31])[N:26]([CH2:27][CH2:28][N:17]1[CH2:16][CH2:15][N:14]([C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:13][CH:12]=[CH:11][N:10]=2)[CH2:19][CH2:18]1)[CH3:30])([CH3:23])([CH3:22])[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazine

生成物 1

HCID 67366867{2-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-carbamic acid tert-butyl ester収率 97%

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒

実験手順

Dissolve 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (2.5 g, 9.7 mmol, 1 eq.) in 1,2 dichloroethane (20 mL). Add methyl-(2-oxo-ethyl)-carbamic acid tert-butyl ester (1.77 g, 10.19 mmol, 1.05 eq.). Add sodium triacetoxy-borohydride (3.10 g, 14.6 mmol, 1.5 eq.). Stir at room temperature for 18 hr. Partition the reaction mixture between aqueous saturated NaHCO3 and dichloromethane. Separate the layers. Extract the organic layer with dichloromethane (2×100 mL). Combine the organic layers, dry over anhydrous Na2SO4, filter and concentrate. Purify by normal phase chromatography with 30% EtOAc/hexane—100% EtOAc to afford the title preparation (3.8 g, 97% yield). MS (loop): m/z=416.3 [M+H].

後処理

  1. customPartition the reaction mixture between aqueous saturated NaHCO3 and dichloromethane
  2. customSeparate the layers
  3. extractionExtract the organic layer with dichloromethane (2×100 mL)
  4. dry with materialCombine the organic layers, dry over anhydrous Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by normal phase chromatography with 30% EtOAc/hexane—100% EtOAc
  8. customto afford the title
  9. custompreparation (3.8 g, 97% yield)

出典と根拠

ORDレコード
ord-bc57a883d1e3446f963f46a2710f6866
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048884B2

反応ノート

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