Aniline → N-phenyl-2(S)-(tert-butoxycarbonylamino)-3-phenylpropanamine

HRID 342627Notes

Reaction equation

HRID 342627 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:17]=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:2]1([NH:1][CH2:17][C@@H:16]([NH:15][C:13]([O:12][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:14])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Product 1

HCID 10568153N-phenyl-2(S)-(tert-butoxycarbonylamino)-3-phenylpropanamine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Aniline (3.00 mL, 32.9 mmol) was dissolved in dichloroethane under nitrogen. The product from Step B was added (7.0 g, 29.91) and the reaction stirred for 1 h at room temperature. Sodium triacetoxyborohydride (9.51 g, 44.86 mmol) was added, and the pH adjusted to 5. The reaction was stirred overnight, then quenched with saturated sodium bicarbonate solution. The aqueous layer was removed, the organic phase washed with saturated brine and dried over magnesium sulfate. The title compound was obtained after chromatography on silica get with 8% ethyl acetate in hexane.

Workup

  1. stirringThe reaction was stirred overnight
  2. customquenched with saturated sodium bicarbonate solution
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-f57ec193bbda4bb2aa202df914e8578b
Source dataset
uspto-grants-1999_01
Patent number
US05859012

Reaction notes

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