Acetic Acid → HCID 89714590, compound

HRID 2273066Notes

Reaction equation

HRID 2273066 reaction equation
[NH2:1][CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].C(O)(=O)C.[C:11]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH:20]=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[C:14]([O:13][C:11]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][NH:1][CH2:2][C:3]([OH:5])([CH3:6])[CH3:4])=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 951022-Propanol, 1-amino-2-methyl-HCID 516892Sodium BicarbonateHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 89714590HCID 89714590, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4.34 g of 1-amino-2-methylpropan-2-ol (48.68 mmol) are placed in 50 ml of MeOH. 2.79 ml of acetic acid (48.68 mmol) and then 4.72 ml of N-Boc-L-prolinal (24.34 mmol), diluted beforehand in 20 ml of MeOH, are successively added dropwise. The reaction mixture is stirred at room temperature for 30 minutes and 3.22 g of sodium cyanoborohydride (48.68 mmol) are then added portionwise. After stirring at room temperature for 18 hours, the medium is poured into 400 ml of saturated aqueous NaHCO3 solution. The aqueous phase is extracted with 3 times 150 ml of DCM. The organic phases are combined, washed with 200 ml of water, with 200 ml of brine, dried over MgSO4, filtered and evaporated. 7.19 g of (S)-2-[(2-hydroxy-2-methyl propylamino)methyl]pyrrolidine-1-carboxylic acid tert-butyl ester are obtained.

Workup

  1. additionare successively added dropwise
  2. stirringAfter stirring at room temperature for 18 hours
  3. extractionThe aqueous phase is extracted with 3 times 150 ml of DCM
  4. washwashed with 200 ml of water, with 200 ml of brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-bdb8415973344816936ba4985d991acd
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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