Ammonium Hydroxide → (5-Aminopentyl)(phenylmethoxy)carbamic acid tert-butyl ester

HRID 2380431Notes

Reaction equation

HRID 2380431 reaction equation
[NH4+].[OH-].[C:3]([O:7][C:8]([N:10]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>[Ni].CO>[NH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 10685938tert-Butyl benzyloxy(4-cyanobutyl)carbamate

Product 1

HCID 10979777(5-Aminopentyl)(phenylmethoxy)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

N-(5-Aminopentyl)-N-(tert-butoxycarbonyl)-O-benzylhydroxylamine (7) was prepared by adding Raney nickel (W-2 grade, 0.98 g) and concentrated NH4OH (1.6 mL) to a solution of (4) (0.57 g, 1.87 mmol) in methanol (9.5 mL) in a 250 mL Parr bottle. The suspension was cooled to 0° C. and ammonia was gently bubbled in for 10 minutes. Hydrogenation was carried out on a Parr shaker for 3.5 hours at 55-58 psi. The catalyst was filtered off (Celite) and the filtrate was concentrated to give 0.61 g crude product. Column chromatography using 5% concentrated NH4OH/CH3OH yielded 0.48 g of (7) (83% yield): NMR δ 1.25-1.72 (m, 17 H), 2.64 (t, 2 H, J=7), 3.39 (t, 2 H, J=7), 4.78 (s, 2 H), 7.31 (s, 5 H). Anal. calcd. for C17H28N2O3 : C, 66.21; H, 9.15; N, 9.08. Found: C, 66.24, H, 9.18; N, 9.05.

Workup

  1. customammonia was gently bubbled in for 10 minutes
  2. filtrationThe catalyst was filtered off (Celite)
  3. concentrationthe filtrate was concentrated
  4. customto give 0.61 g crude product

Sources & evidence

ORD record
ord-cb787ce9bec544f2af806625fae324d9
Source dataset
uspto-grants-1994_11
Patent number
US05367113

Reaction notes

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