Acetic Acid → 2-[2-Phenylpropylamino]ethyl carbamic acid tert-butyl ester

HRID 609654Notes

Reaction equation

HRID 609654 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[C:12]1([CH:18]([CH3:21])[CH:19]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH:10][CH2:19][CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 71462-PhenylpropanalHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 675750332-[2-Phenylpropylamino]ethyl carbamic acid tert-butyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the same way as that described in Example 4, Step 1, using tert-butyl-N-(2-aminoethyl)carbamate (1.6 g, 10 mmol), 2-phenylpropionaldehyde (1.32 mL, 10 mmol), MeOH (100 mL), acetic acid (1.72 mL, 30 mmol) and sodium cyanoborohydride (1.26 g, 20 mmol). The crude residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (90:10), to give the amine (1.56 g, 56%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ1.26 (3H, d, J=6.9 Hz), 1.42 (9H, s), 2.70-2.81 (4H, m), 2.90-3.00 (1H, m), 3.14-3.24 (2H, m), 4.89 (1H, br s), 7.19-7.35 (5H, m).

Workup

  1. customThe crude residue was chromatographed on silica gel
  2. washeluting with CH2Cl2 :MeOH (90:10)

Sources & evidence

ORD record
ord-b0e85706d5294622805ce376a784d752
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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