Borane;tetrahydrofuran → 3-Tert-butoxycarbonyl-5-hydroxymethylthiazolidine

HRID 350520Notes

Reaction equation

HRID 350520 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12](C(O)=O)[CH2:11][S:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1C[O:20][CH2:19]C1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:19][OH:20])[S:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 51470143-(1,1-Dimethylethyl) 3,4-thiazolidinedicarboxylate

Product 1

HCID 235121323-Tert-butoxycarbonyl-5-hydroxymethylthiazolidineYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-tert-butoxycarbonylthiazolidine4-carboxylic acid (2.3 g, 10.0 mmol) in THF (30 ml) was added BH3.THF(1.0 M solution in THF, 20.0 ml, 20.0 mmol) at 0° C. After stirred at room temperature for 1.0 h, the reaction mixture was heated under reflux for 1.0 hr. 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 3-tert-butoxycarbonyl-5-hydroxymethylthiazolidine (2.0 g , quant) as a a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9H), 2.80–2.85 (m, 1H), 3.13–3.17 (m, 1H), 3.20–3.30 (m, 1H), 3.64–3.70 (m, 2H), 4.34 (br s, 1H), 4.60 (br s, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1.0 hr
  3. temperatureAfter cooled
  4. concentrationthe mixture was concentrated in vacuo
  5. additionWater was added
  6. extractionat 0° C., and extracted with EtOAc
  7. washThe extract was washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34b7641d56c844b29f664f8297c0b164
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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