tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate → trans-3-methoxy-4-hydroxy-1-Boc-Pyrrolidine

HRID 1896211Notes

Reaction equation

HRID 1896211 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][O-:15].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([O:15][CH3:14])[C@H:12]([OH:11])[CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 14948608trans-3-methoxy-4-hydroxy-1-Boc-Pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3 g, 16 mmol) was dissolved in 2-Me-THF (10 mL) and a solution of sodium methoxide in methanol (10 mL of a 25% solution) was added and the reaction stirred at rt overnight. Reaction was quenched with sat. NH4Cl and concentrated, then after extraction with EtOAc, residue was purified by column chromatography on SiO2 (35% EtOAc/heptane) which gave the title compound IIa as a clear oil (1.05 g).

Workup

  1. customReaction
  2. customwas quenched with sat. NH4Cl
  3. concentrationconcentrated
  4. extractionafter extraction with EtOAc, residue
  5. customwas purified by column chromatography on SiO2 (35% EtOAc/heptane) which

Sources & evidence

ORD record
ord-8f9983b0961a485daf4241c55107163a
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

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