Ethyl Acetate → 3-(1-Aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester

HRID 10349

Reaction equation

HRID 10349 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][C:13]2([O:15][CH:14]2[CH3:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[OH-].[NH4+:26]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][C:13]([CH:14]([NH2:26])[CH3:16])([OH:15])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 21041146Benzyl 2-methyl-1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

Product 1

HCID 690686403-(1-Aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methyl-1-oxa-5-azaspiro[2,4]heptane-5-carboxylic acid benzyl ester (Example A9, 0.31 g, 1.25 mmol) in methanol (10 mL) and ammonium hydroxide (7 mL) is heated in a sealed tube at 100° C. for 16 hours. After cooling, the reaction mixture is dissolved ethyl acetate, washed with water, dried over Na2SO4 and evaporated to afford the title compound (0.340 g). 1H NMR (200 MHz, CDCl3): δ 7.33–7.26 (m, 5H), 5.28 (bs, 2H), 5.07 (s, 2H), 3.56–3.16 (m, 5H), 2.03–1.76 (m, 2H), 1.15 (d, 3H).

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-25d841ff62cf41b6862babb19ab9536f
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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