Hydrochloric Acid → 1-Boc-3-pyrrolidinol

HRID 2421963Notes

Reaction equation

HRID 2421963 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[BH4-].[Na+].Cl>CO.O>[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 44169391-Boc-3-pyrrolidinolYield 98.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3-oxopyrrolidine-1-carboxylate (3.00 g, 16.20 mmol) was dissolved in dry MeOH (60 mL) and cooled in an ice-water bath. Sodium borohydride (0.61 g, 16.20 mmol) was added carefully and the reaction mixture was stirred at 0° C. for 15 mins. The reaction mixture was diluted with water and pH was set to −9 with HCl (1% aqueous solution). The aqueous layer was extracted with EtOAc and the organic layers were combined, dried with MgSO4, filtered and evaporated to give the title compound (3.00 g, 98.9%). 1H NMR (500 MHz, CDCl3): δ 1.42 (s, 9H), 1.85-1.96 (m, 2H), 3.26-3.33 (m, 2H), 3.38-3.47 (m, 3H), 4.38-4.40 (m, 1H); 13C NMR (125 MHz, CDCl3): δ 28.72, 33.95, 43.99, 54.38, 70.60, 79.57, 155.07.

Workup

  1. temperaturecooled in an ice-water bath
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d5ab152dee50491790df752de6220e8e
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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