Borane → tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate

HRID 1396020Notes

Reaction equation

HRID 1396020 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:13](O)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 110959892-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid

Product 1

HCID 22594530tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution consisting of 3-carboxymethyl-azetidine-1-carboxylic acid tert-butyl ester (10.0 g, 46.5 mmol) and THF (15 mL) was cooled to 0° C. and treated with a 1 M solution of borane in THF (70 mL, 70 mmol), then slowly warmed to rt. After stirring for 18 h, the reaction mixture was quenched with 2 N NaOH (100 mL), diluted with H2O (100 mL), and extracted with Et2O (3×200 mL). The organic layers were combined, dried (MgSO4), and concentrated to give the title compound as a colorless oil (9.03 g, 97%). MS (ESI+): calcd. for C10H19NO3, 201.14. m/z found, 224.2 (M+Na)+. 1H NMR (d6-DMSO): 4.37 (t, J=5.1 Hz, 1H), 3.95-3.79 (m, 2H), 3.53-3.43 (m, 2H), 3.37 (dd, J=11.5, 6.2 Hz, 2H), 2.62-2.52 (m, 1H), 1.66 (dd, J=13.8, 6.4 Hz, 2H), 1.39-1.33 (m, 9H).

Workup

  1. temperatureslowly warmed to rt
  2. customthe reaction mixture was quenched with 2 N NaOH (100 mL)
  3. additiondiluted with H2O (100 mL)
  4. extractionextracted with Et2O (3×200 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89d758840cc4499d9648aa0c6c7870c2
Source dataset
uspto-grants-2014_12
Patent number
US08901111B2

Reaction notes

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