Tert-butyl 2-[4-(dibenzylamino)cyclohexoxy]acetate → Tert-butyl 2-(4-aminocyclohexoxy)acetate

HRID 1772289Notes

Reaction equation

HRID 1772289 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 58206858Tert-butyl 2-[4-(dibenzylamino)cyclohexoxy]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 10680931Tert-butyl 2-(4-aminocyclohexoxy)acetateYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Tert-butyl 2-[4-(dibenzylamino)cyclohexoxy]acetate (6 g, 15 mmol, 1 eq.) was dissolved in methanol (200 mL) and pumped through the H-Cube® hydrogenation instrument containing a 10% Pd(OH)2 catalyst cartridge (CatCart) and using full hydrogen flow, ambient pressure, at 40° C. for 3 hours. The solvent was removed under vacuum to provide tert-butyl 2-(4-aminocyclohexoxy)acetate (3.3 g, 98%); (CI, m/z): [M+H]+ 230; 1H NMR (400 MHz, CDCl3): δ 3.99 (s, 2H), 3.31 (tt, J=10.7, 4.2 Hz, 1H), 2.71 (tt, J=10.8, 3.9 Hz, 1H), 2.00-2.11 (m, 2H), 1.83-1.93 (m, 2H), 1.46-1.51 (m, 9H), 1.29-1.44 (m, 4H), 1.06-1.19 (m, 2H).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ad4d6ef7f9514cb6bf71b08b475ac5e6
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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