{(S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-carbamic acid benzyl ester → (S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propylamine

HRID 1182094Notes

Reaction equation

HRID 1182094 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH2:26][O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:12][CH2:13][N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:15]1)C1C=CC=CC=1>CO>[C:28]([O:27][CH2:26][C@@H:11]([NH2:10])[CH2:12][CH2:13][N:14]1[CH2:15][CH:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:17]1)([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 1

HCID 69410844{(S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-carbamic acid benzyl ester

Product 1

HCID 69411039(S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {(S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-carbamic acid benzyl ester (0.2 g, 0.45 mmol) in methanol containing 10% palladium on carbon (66 mg) is stirred under an atmosphere of hydrogen for 3 hours, then filtered through a celite™ filter The filtrate is evaporated and the residue taken up in ethyl acetate, washed with aqueous NaHCO3 solution and brine, dried over MgSO4 and evaporated to afford (S)-1-tert-butoxymethyl-3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propylamine.

Workup

  1. filtrationfiltered through a celite™
  2. filtrationfilter The filtrate
  3. customis evaporated
  4. washwashed with aqueous NaHCO3 solution and brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-05285c997ef6440cb31df08b29cfe57a
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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