Water → Tert-butyl 2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

HRID 1644799Notes

Reaction equation

HRID 1644799 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@:9]1([CH3:16])[C:13](O)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:13][OH:14])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 11206950(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid

Product 1

HCID 23512318Tert-butyl 2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of commercially available (S)-2-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (5 g, 0.021 mol) dissolved in DCM (150 mL) was added BH3-DMS (3.3 mL 0.043 mol) at 0° C., dropwise over the course of 45 min with stirring. The reaction mixture was stirred for 5 h at room temperature. The reaction mixture was treated with DCM (150 mL) and water (50 mL). The organic layer was isolated, washed with saturated NaHCO3 solution (2×50 mL) followed by brine (2×50 mL), dried (anhydrous Na2SO4), and concentrated using rotary evaporator to give desired (rac)-2-hydroxymethyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester yellowish brown liquid (4.0 g, 86%).

Workup

  1. stirringThe reaction mixture was stirred for 5 h at room temperature
  2. customThe organic layer was isolated
  3. washwashed with saturated NaHCO3 solution (2×50 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customevaporator

Sources & evidence

ORD record
ord-56d5d819b725462393df7e25223d3a48
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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