Hydrochloric Acid → Ethyl 1-Boc-4-hydroxypyrrolidine-3-carboxylate

HRID 2302116Notes

Reaction equation

HRID 2302116 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:10](=[O:11])[CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S([O-])(=O)=O)=CC=2)=CC=1)C.[Na+].Cl>CO>[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([OH:11])[CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 108689421-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylateHCID 23673835C.I. Acid Orange 52

Product 1

HCID 53400859Ethyl 1-Boc-4-hydroxypyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.15 g (20 mmol) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester in 30 ml methanol was added 1.88 g (30 mmol) sodium cyanoborohydride and a small amount of methylorange. With stirring the pH was adjusted to 3 by dropwise addition of 1N hydrochloric acid (color change from yellow to orange). After no more acid was consumed the mixture was stirred for one hour. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed twice with water, then with brine, dried over magnesium sulfate and evaporated. The residual yellow oil was used in the next step without any further purification.

Workup

  1. customAfter no more acid was consumed the mixture
  2. stirringwas stirred for one hour
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed twice with water
  6. dry with materialwith brine, dried over magnesium sulfate
  7. customevaporated
  8. customThe residual yellow oil was used in the next step without any further purification

Sources & evidence

ORD record
ord-7d332dbb82aa43b790dd32ff281983bc
Source dataset
uspto-grants-2002_08
Patent number
US06429288B1

Reaction notes

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