(1S,4S)-1-(2-Benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester → 1-(2-Hydroxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid tert-butyl ester

HRID 1804766Notes

Reaction equation

HRID 1804766 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]2[CH2:14][CH2:15][C@:10]([CH2:16][CH2:17][O:18]CC3C=CC=CC=3)([CH:11]=[CH:12]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:12][CH2:11][C:10]([CH2:16][CH2:17][OH:18])([CH2:15][CH2:14]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59152652(1S,4S)-1-(2-Benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester

Product 1

HCID 591526601-(2-Hydroxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

1 g Pd—C is placed into an round-bottom flask under an argon atmosphere and covered with ethanol. A solution of (1S,4S)-1-(2-benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester (10) (2 g, 5.8 mmol) in 58 ml of ethanol is added and the mixture is hydrogenated at rt for 6 h. Then the mixture is filtrated over celite and evaporated under reduced pressure. The product was used in the next step without further purification.

Workup

  1. filtrationThen the mixture is filtrated over celite
  2. customevaporated under reduced pressure
  3. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-6aa7d935300846b8b3a285b079372ed2
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

Loading…