Borane;tetrahydrofuran → 4-Fluoro-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 350459Notes

Reaction equation

HRID 350459 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([F:13])[CH2:10][CH:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([F:13])[CH2:10][CH:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 47125231-(Tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Product 1

HCID 569735834-Fluoro-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, 4.7 mmol) in THF (10.0 ml) was added BH3.THF(1.0 M solution in THF, 10.0 ml, 10.0 mmol) at 0° C. After stirred at room temperature for 1.0 h. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (1.0 g, quant) as a a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9H), 2.29–2.39 (m, 1H), 3.38–3.59 (m, 2H), 3.74–3.88 (m, 2H), 4.09–4.14 (m, 2H), 4.85 (m, 1H), 5.03 (br s, 1H), 5.16 (br s, 1H).

Workup

  1. temperatureAfter cooled
  2. concentrationthe mixture was concentrated in vacuo
  3. additionWater was added
  4. extractionat 0° C., and extracted with EtOAc
  5. washThe extract was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee9b96ed53dd46be9218cbf162712a4c
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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