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

HRID 1466023Notes

Reaction equation

HRID 1466023 reaction equation
[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]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 772306645-Formyl-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-31ddb32677ab412cb1c035f020e82260
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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