Hydrochloric Acid → 2-(Hydroxymethyl)-4-(methanesulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1792032Notes

Reaction equation

HRID 1792032 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O.[BH4-].[Li+].Cl>O1CCCC1>[C:18]([O:17][C:15]([N:6]1[CH2:7][CH:8]([O:10][S:11]([CH3:14])(=[O:12])=[O:13])[CH2:9][CH:5]1[CH2:3][OH:2])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2×HCID 147726801-Tert-butyl 2-methyl 4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 214612722-(Hydroxymethyl)-4-(methanesulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl esterYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1.972 g) was dissolved in tetrahydrofuran (40 ml), and lithium borohydride (300 mg) was added thereto. The reaction mixture was stirred at room temperature overnight, additional lithium borohydride (1000 mg) was added, and the mixture was stirred at room temperature for 2 hours. 1 N Hydrochloric acid was added to the reaction solution, and then was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 1.715 g of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58313497266c441c9a701507bdd5b267
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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