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Acetic Acid → Tert-butyl (2-{[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate

HRID 1466023
ノート
印刷プレビュー

反応式

HRID 1466023 の反応式
[CH:1]([CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([C:13]#[N:14])=[CH:7][CH:6]=[CH:5][C:4]1=2)=O.[C:15]([O:19][C:20](=[O:25])[NH:21][CH2:22][CH2:23][NH2:24])([CH3:18])([CH3:17])[CH3:16].CC(O)=O.[BH3-]C#N.[Na+]>CO.C(Cl)Cl.O>[C:13]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH2:10][CH2:11][CH2:12][CH:3]2[CH2:1][NH:24][CH2:23][CH2:22][NH:21][C:20](=[O:25])[O:19][C:15]([CH3:18])([CH3:16])[CH3:17])#[N:14]
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 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 772306645-Formyl-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

生成物 1

HCID 131732671Tert-butyl (2-{[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
2 回
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-Formyl-5,6,7,8-tetrahydronaphthalene-1-carbonitrile (0.30 g, 1.6 mmol) in MeOH (8 mL) was added (2-amino-ethyl)-carbamic acid tert-butyl ester (0.26 g, 1.6 mol) in MeOH (8 mL), followed by AcOH (0.29 g, 4.8 mmol) and NaBH3CN (0.20 g, 3.2 mmol). The reaction mixture was stirred 2-3 h, and then water (20 mL) and DCM (20 mL) was added. Extracted with DCM, and the organic layers were dried over anhydrous Na2SO4, evaporate to give the crude product, which was purified by column to give the title compound. MS m/z: 330 [M+1]+.

後処理

  1. extractionExtracted with DCM
  2. dry with materialthe organic layers were dried over anhydrous Na2SO4
  3. customevaporate
  4. customto give the crude product, which
  5. customwas purified by column

出典と根拠

ORDレコード
ord-31ddb32677ab412cb1c035f020e82260
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08999990B2

反応ノート

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